Sodium borohydride → (4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)methanol

Temperature

0 °C

To a solution of 4-(4-chloro-2-fluorophenyl)nicotinaldehyde (3 g, 12.73 mmol) in a mixture of methanol (5 mL) and tetrahydrofuran (5 mL) cooled to 0° C. was added NaBH4 (0.722 g, 19.10 mmol) and the solution stirred for 30 min. The reaction was quenched by addition of water (10 mL). The solution was extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL), dried with sodium sulfate and concentrated under reduced pressure to yield (4-(4-chloro-2-fluorophenyl)pyridin-3-yl)methanol that was used without further purification in the next step. LCMS (ESI) m/e 238 [(M+H)+, calcd for C12H10ClFNO 238.0].

1. customThe reaction was quenched by addition of water (10 mL)
2. extractionThe solution was extracted with ethyl acetate (3×15 mL)
3. washThe combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL)
4. dry with materialdried with sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-56d0ed09e7074d2aa6823c23cf2a9d9f

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969564B2