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

HRID 709630Notes

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. To the reaction mixture was added a solution of methyl 6-chloro-5-(2-fluoro-5-methoxyphenyl)picolinate (8.30 g) in ethanol (25 ml) and THF (50 ml) 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. This compound was used for the next step without further purification.

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-fefe91cc24ce4127a5a76dba3b9f2247
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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