Hydrochloric Acid → (6-Chloro-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol

HRID 1049523Notes

Reaction equation

[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[Cl:6][C:7]1[N:12]=[C:11]([C:13](OC)=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[F:25].Cl.C(=O)([O-])O.[Na+]>C(O)C.C1COCC1>[Cl:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[F:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, to a suspension of calcium chloride (12.3 g) in ethanol (100 mL) and THF (50 mL) was added sodium tetrahydroborate (2.62 g) at 0° C., and the mixture was stirred at 0° C. for 10 min. A solution of methyl 6-chloro-5-(2-fluoro-5-methoxyphenyl)picolinate (8.30 g) in ethanol (25 mL) and THF (50 mL) was added at room temperature and the mixture was stirred for 14 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was neutralized with aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (7.30 g) as a pale-gray amorphous solid.

Workup

stirringthe mixture was stirred for 14 hr
extractionThe reaction mixture was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-cc74c3fff66e4d579075a9e56a1ea4b7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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