Sodium Hydroxide → HCID 68328727, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-fluoro-4-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)benzamide (200 mg, 0.375 mmol) in 1,4-dioxane (3.75 mL) was added aq. NaOH (7 M, 3.75 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 (eluting with 20-80% ACN in water with 0.1% TFA in each solvent) to give 3-fluoro-4-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)benzamide (65 mg, 46%). MS (ESI, pos. ion) m/z: 380.1 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.07 (brs, 2H), 7.74-7.83 (m, 4H), 7.51-7.69 (m, 4H), 3.65-3.75 (m, 1H), 1.19 (d, 6H, J=6.6 Hz).

Provenance & Evidence