Sodium Hydroxide → HCID 68328127, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylbenzamide (250 mg, 0.457 mmol) in 1,4-dioxane (5 mL) was added aq. NaOH (7 M, 5 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 purified with preparative HPLC (eluted with 20-80% MeCN in water with 0.1% TFA in each solvent) to give 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylbenzamide (23 mg, 12%). MS (ESI, pos. ion) m/z: 394.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 11.90 (s, 1H), 8.56 (d, 1H, J=4.8 Hz), 8.16 (dd, 1H, J=7.2, 2.4 Hz), 8.01 (s, 1H), 7.81-7.84 (m, 2H), 7.70 (dd, 1H, J=8.8, 1.2 Hz), 7.60-7.63 (m, 2H), 7.46 (dd, 1H, J=10.4, 8.8 Hz), 3.68-3.76 (m, 1H), 2.81 (d, 3H, J=4.4 Hz), 1.20 (d, 6H, J=6.8 Hz).

Provenance & Evidence