Sodium borohydride → (5-Fluoro-3-methylpyridin-2-yl)methanol

Sodium borohydride (125 mg, 3.3 mmol) was added to a solution of 5-fluoro-3-methylpyridine-2-carbaldehyde (417 mg, 3.0 mmol) in EtOH (10 mL) and stirred at rt for 3 h. The reaction was quenched by dropwise addition of saturated aqueous NH4Cl solution (10 mL) and stirred for 15 h. The reaction mixture was extracted twice with DCM and the combined organic phases were concentrated in vacuo. Purification by gradient column chromatography, eluting with 10-60% EtOAc in iso-hexane to yield the title compound (218 mg, 51%).

1. customThe reaction was quenched by dropwise addition of saturated aqueous NH4Cl solution (10 mL)
2. stirringstirred for 15 h
3. extractionThe reaction mixture was extracted twice with DCM
4. concentrationthe combined organic phases were concentrated in vacuo
5. customPurification by gradient column chromatography
6. washeluting with 10-60% EtOAc in iso-hexane

ORD record

ord-7311e09d06f14b2cbe904d3140519e13

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249160B2