Sodium borohydride → HCID 67956181, compound

Participants

Reaction Steps

To a suspension of 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-5-chloropyridine-3-carbaldehyde (32, 722 mg, 1.77 mmol, 1.0 equiv.) in EtOH (17.7 mL), was added slowly NaBH4 (101 mg, 2.66 mmol, 2.0 equiv.). The reaction mixture was stirred at room temperature until LCMS showed only the desired product. The solvent was evaporated in vacuo. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The extracted organic layers were dried over Na2SO4, filtered and concentrated to give the crude product which was purified with normal phase silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to obtain product 195 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 2H); 7.57 (d, J=8.8 Hz, 1H); 7.38 (d, J=8.8 Hz, 1H); 4.96 (d, J=5.3 Hz, 2H); 4.52 (d, J=7.1 Hz, 2H); 1.43 (m, 1H); 0.69 (m, 2H); 0.52 (m, 2H). LRMS m/z (M+H) 408.9 and 410.9 found, 408.0 and 410.0 required.

Provenance & Evidence