Sodium Hydroxide → HCID 178448830, compound

Participants

Reaction Steps

2-methyl-2-[2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl]butanenitrile (82 mg, 0.2894 mmol) was suspended in a solution of NaOH (46.32 mg, 1.158 mmol) in Water (5.000 mL). The mixture was sonicated to give smaller particle size and cooled in an ice-bath. Sodium hypochlorite (282.8 μL of 8% w/v, 0.3039 mmol) was added slowly dropwise over 2 minutes and the resultant mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with saturated aqueous Na2CO3 and then extracted twice with EtOAc. The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (1:1, Petroleum ether/EtOAc) to give the pure compound as a white solid (3.9 mg, 4% Yield). 1H NMR (DMSO, 400 MHz) δ 0.93 (3H, t), 1.76 (3H, s), 1.99-2.21 (2H, m), 7.54 (1H, s), 8.00 (1H, s), 8.71 (1H, s), 14.29 (1H, br s); MS (ES+) 318.08

Provenance & Evidence