Sodium borohydride → [6-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazin-3-yl]methanol

Participants

Reaction Steps

Sodium borohydride (14.0 mg, 0.362 mmol) was added to a stirred solution of 5c (113 mg, 0.241 mmol) in EtOH (2.00 mL) at 0° C., and the resulting mixture was allowed to warm to rt. After approximately 12 h, the reaction mixture was cooled to 0° C. and quenched by the addition of aqueous 1N HCl. The resulting mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 30%-100% EtOAc/hexanes as eluent) afforded the title compound 5d. m/z (ES) 441 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.61 (d, 1H, J=3.2 Hz), 8.40 (m, 1H), 7.97 (d, 2H, J=8.2 Hz), 7.83 (d, 1H, J=8.7 Hz), 7.75 (m, 1H), 7.52 (m, 4H), 7.26 (m, 1H), 7.19 (m, 2H), 5.23 (s, 2H), 3.09 (m, 1H, J=6.6 Hz), 1.72 (s, 3H), 0.88 (d, 3H, J=6.6 Hz), 0.83 (d, 3H, J=6.6 Hz).

Provenance & Evidence