Sodium borohydride → HCID 71008484, compound

Participants

Reaction Steps

To a cooled (ice bath) flask containing 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-formylphenyl)-1H-indole-3-carboxamide (51 mg, 0.11 mmol) dissolved in methanol/dichloromethane (1.35 ml, 2.9:1) was added a solution of sodium borohydride (20 mg, 0.53 mmol) in water (0.35 ml), via slow drop-wise addition. The mixture was stirred for 10 minutes and then taken up in dichloromethane (20 ml) and water (20 ml). The contents were poured into a separatory funnel and agitated. The organic phase was collected and washed with a solution of 50% diluted brine (20 ml). The dichloromethane layer was collected and the aqueous phases were back extracted with methylene chloride (2×20 mL). The organic phases were combined, dried over magnesium sulfate, filtered and stripped. The crude material was purified by filtration through a short column of silica gel, eluting with 7.5% methanol/dichloromethane. The desired fraction was collected and then the material was crystallized from a solution of hot dichloromethane/hexanes to provide white crystalline product as 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-1H-indole-3-carboxamide (37 mg). LC/MS calcd for C28H25FN4O3 (m/e) 484.54, obsd 485.0 (M+H, ES+): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9H) 4.03-4.37 (m, 2H) 5.49-6.00 (br. s, 2H) 7.18-7.38 (m, 3H) 7.49-7.71 (m, 5H) 8.13-8.28 (m, 2H) 8.32 (d, J=2.64 Hz, 1H).

Provenance & Evidence