Sodium borohydride → HCID 86695915, compound

To a stirred solution of 2-amino-4-(4-chloro-2-fluorophenyl)nicotinaldehyde (50 mg, 0.199 mmol) in MeOH (2 mL) and THF (5 mL) was added sodium borohydride (9.06 mg, 0.239 mmol) then the solution was stirred for 1 h. The volatile organics were removed under reduced pressure and the residue was quenched by addition of saturated aqueous ammonium chloride solution (10 mL). The reaction mixture was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were washed with brine (1×10 mL), dried over sodium sulfate and concentrated under reduced pressure to yield (2-amino-4-(4-chloro-2-fluorophenyl)pyridin-3-yl)methanol (50 mg, 0.198 mmol, 21% yield for two steps). LCMS (ESI) m/e 253 [(M+H)+, calcd for C12H11ClFN2O 253.0]; LC/MS retention time (Method C): tR=1.48 min.

1. customThe volatile organics were removed under reduced pressure
2. customthe residue was quenched by addition of saturated aqueous ammonium chloride solution (10 mL)
3. extractionThe reaction mixture was extracted with CH2Cl2 (2×10 mL)
4. washThe combined organic extracts were washed with brine (1×10 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-edd79ccfe3d3414fa913ac14d099ef0b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703953B2