Sodium borohydride → HCID 90386113, compound

Participants

Reaction Steps

To a solution of 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinaldehyde (30.0 mg, 0.0740 mmol) in methanol (25 mL) was added NaBH4 (8.40 mg, 0.220 mmol). Reaction mixture was stirred at room temperature for 3 h and diluted with cold water (50 mL). The aqueous solution was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with saturated brain solution, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 12 g, 40% EtOAc/hexanes) to get (5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)methanol (15.0 mg, 50.0%). LCMS Condition B-12: retention time 2.15 min, [M+1]=406.2. HPLC Condition B-2: retention time 9.20 min, Purity 98.03%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.64 (d, J=5.7 Hz, 2H), 4.82 (d, J=5.7 Hz, 2H), 5.45 (t, J=5.7 Hz, 1H), 6.64 (t, J=5.2 Hz, 1H), 6.80 (d, J=2.7 Hz, 1H), 7.22-7.55 (m, 10H), 7.90 (d, J=2.7 Hz, 1H), 8.49 (t, J=2.1 Hz, 1H), 8.59 (d, J=2.0 Hz, 1H), 9.24 (d, J=2.0 Hz, 1H).

Provenance & Evidence