1242156-59-7 | Page 8 of 10 | Heterocyclic Building Blocks-phthalazine

Application of 1242156-59-7

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A common heterocyclic compound, the phthalazine compound, name is 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,cas is 1242156-59-7, mainly used in chemical industry, its synthesis route is as follows.,1242156-59-7

Step 2. In a 25 mL container, 1-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrile (50 mg, 181 mumol, Eq: 1.00), 6-tert-butyl-8-fluorophthalazin-1(2H)-one (79.8 mg, 362 mumol, Eq: 2) and copper (I) iodide (69.0 mg, 362 mumol, Eq: 2.00) were combined with DMSO (2.00 ml) to give a yellow suspension. Sodium bicarbonate (38.0 mg, 453 mumol, Eq: 2.5) was added to it. The mixture was heated in a microwave at 120 C. for 1 hr. The reaction mixture was poured into 25 mL sat NH4Cl and extracted with EtOAc (3¡Á25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The organic layer was concentrated and purified through ISCO flash column chromatography using ethyl acetate (containing 5% methanol) in hexanes (5% to 80% linear gradient in 15 minutes, 12 g silica gel) to give the pure desired product which was triturated with ether in hexanes and filtered to obtain 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-formylphenyl)-1H-pyrazole-3-carbonitrile (19 mg, 25%).

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Reference£º
Patent; Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta; US2012/295885; (2012); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

Application of 4,5-Dimethyl-1,3-dioxol-2-one

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NaH (60%), 108 mg, 2.72 mmol) was added portionwise to a solution of 6-tert-butyl-8-fiuoro- 2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 300.0 mg, 1.36 mmol) in DMF (3 mL) at 0 C. The mixture was heated at 70 C for 30 min. The mixture was cooled to room temperature, a solution of (2-bromo-5- bromomethyl-4-fiuoro-phenyl)-methanol (203 mg, 0.68 mmol) in DMF (2 mL) was added and the mixture was stirred for 2.5 h at room temperature. Water (5 mL) was added, and the mixture was extracted with EtOAc (3 x 15 mL). The combined organic layers were dried (Na2S04), filtered, and evaporated. The residue was purified by preparative HPLC to give 2-(4-bromo-2- fluoro-5-hydroxymethyl-benzyl)-6-tert-butyl-8-fluoro-2H-phthalazin-l-one (59 mg, 10%). MS calcd. for CzoftoB^NzC^ [(M+H)+] 437, obsd. 436.8.

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Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DOMINIQUE, Romyr; LOPEZ-TAPIA, Francisco Javier; MERTZ, Eric; SO, Sung-Sau; WO2014/76104; (2014); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

Analyzing the synthesis route of 1242156-59-7

The synthetic route of 1242156-59-7 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1242156-59-7,6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,as a common compound, the synthetic route is as follows.

Step 5. Preparation of 2-(6-tert-butyl-8-fluoro-l-oxo-lH-phthalazin-2-yl)-4-iodo-pyridine-3- carbaldehyde Method A In a 1 L round-bottomed flask, 6-tert-butyl-8-fluorophthalazin-l(2H)-one (5.6 g, 25.4 mmol) was combined with THF (300 ml) to give a colorless solution. Sodium hydride (1.12 g, 28.0 mmol) was added. The reaction mixture was stirred at ambient temperature for 10 min. 2-Fluoro-4- iodonicotinaldehyde (7.02 g, 28.0 mmol) was added and the reaction mixture was stirred at ambient temperature for 1 h. The reaction was complete as determined by LCMS analysis. The reaction mixture was quenched with saturated NH4CI. The reaction mixture was poured into 200 mL of H20 and extracted thrice with CH2CI2. The organic layers were washed with brine, then dried over Na2S04 and concentrated under vacuum. The resultant bright yellow solid was transferred into a filter funnel and the flask washed twice with a small volume of EtOAc to ensure complete transfer of the solid into the funnel. The liquid was filtered through. The solid was triturated twice with Et20 and dried under vacuum to afford the desired product as a cream- colored solid (8.09 g, 17.9 mmol, 70.5 % yield). (M+H)+ = 452 m/e. *H NMR (400 MHz, CUC -d) delta ppm 1.44 (s, 9 H) 7.49 – 7.54 (m, 1 H) 7.54 (d, 7=1.77 Hz, 1 H) 8.03 (d, 7=5.31 Hz, 1 H) 8.30 (d, 7=2.53 Hz, 1 H) 8.37 (d, 7=5.31 Hz, 1 H) 9.98 (s, 1 H)., 1242156-59-7

The synthetic route of 1242156-59-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; IYER, Raman Mahadevan; LAINE, Dramane Ibrahim; LOPEZ-TAPIA, Francisco Javier; PHILLIPS, Jonathan E.; STEVENSON, Christopher; WO2014/83026; (2014); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

Some tips on 1242156-59-7

1242156-59-7 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one 59473765, aphthalazine compound, is more and more widely used in various.

To a suspension of NaH (60%, 473 mg, 1 1.8 mmol) in DMF (5 mL) was added a solution of 6- tert-butyl-8-fluoro-2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 1.3 g, 5.91 mmol) at 0 C. The mixture was stirred for 5 min at 0 C and heated at 70 C for 30 min under nitrogen. The mixture was cooled to room temperature, a solution of 4-bromo-l-bromomethyl-2-fluoro-benzene (1.74 g, 6.5 mmol) in DMF (3 mL) was added and the mixture was stirred for 1.5 h at room temperature. Cold water (5 mL) was added. The mixture was extracted with EtOAc and the organic extract was dried (Na2S04), and evaporated. The residue was purified by chromatography (silica gel, 20% EtOAc/hexane) to give 2-(4-bromo-2-fluoro-benzyl)-6-tert-butyl-8-fluoro-2H-phthalazin-l-one (1.0 g, 41%) as a yellow solid. MS calcd. for Ci9Hi8BrF2N20 [(M+H)+] 407, obsd. 407.2., 1242156-59-7

1242156-59-7 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one 59473765, aphthalazine compound, is more and more widely used in various.

Brief introduction of 1242156-59-7

The synthetic route of 1242156-59-7 has been constantly updated, and we look forward to future research findings.

1242156-59-7, 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: 1-(3-Bromo-2-formylphenyl)-3-(4-(morpholine-4-carbonyl)phenylamino)-1H-pyrazole-4-carbonitrile (34 mg, 0.0708 mmol), 6-tert-butyl-8-fluorophthalazin-1(2H)-one (31.2 mg, 0.142 mmol), cuprous iodide (27 mg, 0.142 mmol) and sodium bicarbonate (14.9 mg, 0.177 mmol) were combined in 1 mL of DMSO. The solution was degassed with argon and then heated in a microwave at 120 C. for 1 hr. The resulting mixture was extracted with ethyl acetate and ammonium chloride solution. The organic layer was concentrated and purified by flash column chromatography using ethyl acetate (containing 5% methanol) in hexanes (5% to 80% linear gradient in 15 minutes, 12 g silica gel) to give the pure desired product. This material was triturated with ether in hexanes and filtered to give 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carbonitrile (18.2 mg, 41.5% yield) as a pale pink solid. LC/MS clacd for C33H30FN7O3 (m/e) 591.24, obsd 592.0 (M+H, ES+); 1H NMR (400 MHz, DMSO-d6) delta ppm 1.38 (s, 9H), 3.50 (br., 4H), 3.59 (br., 4H), 7.37 (d, J=8.6 Hz, 2H), 7.59 (d, J=8.3 Hz, 1H), 7.65-7.71 (m, 3H), 7.78 (d, J=13.1 Hz, 1H), 7.87-7.93 (m, 2H), 8.08 (s, 1H), 8.58 (d, J=2.3 Hz, 1H), 9.29 (s, 1H), 9.47 (s, 1H)., 1242156-59-7

The synthetic route of 1242156-59-7 has been constantly updated, and we look forward to future research findings.

Downstream synthetic route of 1242156-59-7

As the paragraph descriping shows that 1242156-59-7 is playing an increasingly important role.

1242156-59-7, 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-(2-Formyl-3-iodophenyl)-3-(4-(morpholine-4-carbonyl)phenylamino)-1H-pyrazole-4-carbonitrile (115 mg, 0.218 mmol), 6-tert-butyl-8-fluorophthalazin-1(2H)-one (48 mg, 0.218 mmol), cuprous iodide (41.5 mg, 0.218 mmol) and sodium bicarbonate (36.6 mg, 0.436 mmol) were combined in 2 mL of DMSO. The mixture was thoroughly degassed with argon and stirred in an oil bath preheated to 100 C. for 1 hr. The mixture was extracted with dichloromethane and water. The organic layer was washed with brine, dried over sodium sulfate and filtered. Solvents were evaporated and the residue was purified by flash column chromatography using methanol in dichloromethane (0% to 5% in 16 minutes, 24 g silica gel) to give 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carbonitrile as a pale pink solid (54 mg, 40% yield). LC/MS clacd for C34H30FN7O4 (m/e) 619.23, obsd 620.0 (M+H, ES+); 1H NMR (400 MHz, CDCl3) delta ppm 1.43 (s, 9H), 3.56-3.76 (m, 8H), 6.61 br. s., 1H), 7.40 (d, J=8.6 Hz, 2H), 7.46 (d, J=8.6 Hz, 2H), 7.52 (dd, J=12.4, 1.8 Hz, 1H), 7.55-7.59 (m, 2H), 7.64 (d, J=7.8 Hz, 1H), 7.78 (t, J=8.1 Hz, 1H), 8.16 (s, 1H), 8.32 (s, 1H), 9.97 (s, 1H)., 1242156-59-7

As the paragraph descriping shows that 1242156-59-7 is playing an increasingly important role.

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1242156-59-7 is used more and more widely, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one, cas is 1242156-59-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,1242156-59-7

1518 mg (5.75 mmol) of 2,6-dibromobenzaldehyde, 506 mg (2.30 mmol) of 6-tert-butyl-8-fluoro-2H-phthalazin-1-one, 1499 mg (4.60 mmol) of cesium carbonate, 42 mg (0.22 mmol) of copper(I) iodide, and 115 mg (0.479 mmol) of 4,7-dimethoxy-1,10-phenanthroline were weighed into a 20 mL reaction vial fitted with a stir bar and septum cap. Added 8 mL of anhydrous dioxane. Purged the reaction mixture with nitrogen for 15 min. Stirred at 100 C. for 16 h. Partitioned the reaction mixture between 25 ml, of 10% MeOH/CH2Cl2 and 25 mL of water. Separated phases and extracted the aqueous phase with 25 mL of 10% MeOH/CH2Cl2. Filtered to break the stable emulsion. The combined organic extracts were washed with 75 mL of brine, dried over MgSO4, and the solvent was removed on rotavap. Purified by silica gel flash chromatography using gradient elution with 0?40% EtOAc/hexane to obtain 406 mg of the title compound as a yellow solid. MS (ESI) doublet 403, 405 (M+H)+.

1242156-59-7 is used more and more widely, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

Reference£º
Patent; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

Share a compound : 1242156-59-7

1242156-59-7 is used more and more widely, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one, cas is 1242156-59-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,1242156-59-7

Step 2. In a 25 mL container, 1-(3-bromo-2-formylphenyl)-1H-pyrazole-4-carbonitrile (100 mg, 362 mumol, Eq: 1.00), 6-tert-butyl-8-fluorophthalazin-1(2H)-one (160 mg, 724 mumol, Eq: 2) and copper (I) iodide (138 mg, 724 mumol, Eq: 2.00) were combined with DMSO (2.00 ml) to give a yellow suspension. Sodium bicarbonate (76.1 mg, 906 mumol, Eq: 2.5) was added to it. The mixture was heated in a microwave at 120 C. for 1 hr. The reaction mixture was poured into 25 mL sat NH4Cl and extracted with EtOAc (3¡Á25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The organic layer was concentrated and purified through ISCO flash column chromatography using ethyl acetate (containing 5% methanol) in hexanes (5% to 80% linear gradient in 15 minutes, 24 g silica gel) to give the pure desired product which was triturated with ether in hexanes and filtered to obtain 1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-1H-pyrazole-4-carbonitrile (110 mg, 73%).

1242156-59-7 is used more and more widely, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

Introduction of a new synthetic route about 1242156-59-7

With the rapid development of chemical substances, we look forward to future research findings about 1242156-59-7

6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one, cas is 1242156-59-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,1242156-59-7

To a stirred suspension of NaH (60%, 55 mg, 1.36 mmol) in DMF (5 mL) was added dropwise a solution of 6-tert-butyl-8-fluoro-2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 150.0 mg, 0.68 mmol) in DMF (10 mL) at 0 C. The mixture was heated to 70 C and stirred for 30 min. The mixture was cooled to room temperature, a solution of 4-bromo-l-chloromethyl-2-fluoro-benzene (available from Aldrich; 167.3 mg, 0.75 mmol) in DMF (5 mL) was added and the mixture was stirred for 4 h at room temperature. Aqueous NH4C1 solution was added. The mixture was extracted with EtOAc, and the EtOAc extract was dried, and evaporated. The residue was purified by chromatography (silica gel, 5% EtOAc/hexane) to give 2-(4-bromo-2-fluoro-benzyl)-6-tert-butyl-8-fluoro-2H- phthalazin-l-one (160 mg, 58%) as a white solid. MS calcd. for Ci9Hi8BrF2N20 [(M+H)+] 408, obsd. 408.

With the rapid development of chemical substances, we look forward to future research findings about 1242156-59-7

Introduction of a new synthetic route about 1242156-59-7

With the rapid development of chemical substances, we look forward to future research findings about 1242156-59-7

6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one, cas is 1242156-59-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,1242156-59-7

To a stirred suspension of NaH (60%, 182 mg, 4.54 mmol) in DMF (1 mL) was added dropwise a solution of 6-tert-butyl-8-fluoro-2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 500 mg, 2.27 mmol) in DMF (1.5 mL) at 0 C. The mixture was heated to 70 C and stirred for 30 min. The mixture was cooled to room temperature, a solution of 5-bromo-2-bromomethyl-l,3-difluoro-benzene (715 mg, 2.5 mmol) in DMF (1.5 mL) was added and the mixture was stirred for 4 h at room temperature. The mixture was cooled and cold water (5 mL) was added. The mixture was extracted with EtOAc and the organic extract was dried, and evaporated. The residue was purified by chromatography (silica gel, 5-10% EtOAc/hexane) to give 2-(4-bromo-2,6-difluoro-benzyl)-6-tert-butyl-8-fluoro-2H- phthalazin-l-one (555 mg, 57%) as a yellow solid. MS calcd. for Ci9Hi7BrF3N20 [(M+H)+] 425, obsd. 425.

With the rapid development of chemical substances, we look forward to future research findings about 1242156-59-7