Sodium Hydroxide → HCID 68328897, compound

Participants

Reaction Steps

To a solution of 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylpicolinamide (100 mg, 0.189 mmol) in 1,4-dioxane (2 mL) was added aq.NaOH (7 M, 2 mL) and the reaction was heated at 90° C. for 1 h. The reaction was then quenched with water to get a precipitate. The precipitate was filtered and washed with water (2×100 mL) and dried. The crude product was crystallized from 20% EtOAc in petroleum ether (3×10 mL) to give 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylpicolinamide (16 mg, 23%). MS (ESI, pos. ion) m/z: 377.2 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.67-8.69 (m, 2H), 8.48 (s, 1H), 8.00 (d, 2H, J=4.0 Hz), 7.80-7.82 (m, 1H), 7.69 (dd, 1H, J=8.4, 1.6 Hz), 7.63 (d, 1H, J=8.4 Hz), 7.59 (d, 1H, J=7.6 Hz), 3.71-3.78 (m, 1H), 2.93 (d, 3H, J=4.8 Hz), 1.23 (d, 6H, J=6.4 Hz).

Provenance & Evidence