Sodium borohydride → 6-(2-(Hydroxymethyl)-4-methoxyphenyl)-4-(methylthio)-2,3'-bipyridine-5-carbonitrile

Participants

Reaction Steps

Sodium borohydride (2.2 mg, 0.058 mmol) was added to a solution of 6-(2-formyl-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile (4.3 mg, 0.012 mmol) in methanol (0.45 mL) and dichloromethane (0.450 mL) at room temperature. After 20 min at ambient temperature, the mixture was quenched with TEA (10 μL) and concentrated. Silica gel chromatography, eluting with 0-10% methanol in dichloromethane, gave 6-(2-(hydroxymethyl)-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile as white solid (2.8 mg, 65% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.12 (1H, δ, J=2.01 Hz), 8.72-8.77 (1H, m), 822-8.28 (1H, m), 7.60-7.65 (1H, m), 7.43-7.49 (2H, m), 7.11 (1H, δ, J=2.76 Hz), 6.97-7.02 (1H, m), 4.44 (2H, s), 3.90 (3H, s), 2.72 (3H, s); MS (ES+) 111/Z: 364 (M+H); LC retention time: 3.061 min (analytical HPLC Method A).

Provenance & Evidence