Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate

HRID 404332Notes

Reaction equation

[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T6.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo, diluted with 1N HCl and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-40% EtOAc in hexanes) to yield T6.3 as a colorless solid (0.307 g, 77% yield).

Workup

concentrationThe reaction was then concentrated in vacuo
additiondiluted with 1N HCl
extractionextracted three times with EtOAc
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe organic solvent was removed under reduced pressure
customthe product was purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-43b1815264244558b16c492246cc8fe9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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