Methanol → 4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoic acid

HRID 2206184Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)=[N:10]1.CO.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)=[N:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoate (2.70 g) in a mixed solvent of methanol (20 mL) THF (20 mL) and water (10 mL) was added 8N aqueous sodium hydroxide solution (4.27 mL), and the mixture was stirred at 50° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The aqueous layer was neutralized with 1N hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (2.59 g).

Workup

extractionthe mixture was extracted with ethyl acetate
customwas neutralized with 1N hydrochloric acid at 0° C.
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-142684e8b75f47018211ba4150e0d1e9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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