Cesium carbonate → HCID 71711626, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIATE Z, 36 mg, 0.121 mmol), 2-bromobenzonitrile (32.9 mg, 0.181 mmol, Sigma-Aldrich, St. Louis, Mo.), Xantphos (13.96 mg, 0.024 mmol), Pd2(dba)3 (11.05 mg, 0.012 mmol), cesium carbonate (118 mg, 0.362 mmol), and toluene (1207 n1). The vial was sealed and placed in a 100° C. heating bath for 20 min, then 1,4-dioxane (1 mL) and cesium carbonate (180 mg) were added. The vial was heated overnight at 120° C., then the mixture was diluted with THF, EtOAc, and 1N aq. HCl. The mixture was extracted with EtOAC (3×), and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The product was purified by chromatography on silica gel (12 g column, 0 to 10% MeOH/DCM to give 4-(2-cyanophenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (9.98 mg, 0.025 mmol) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.43 (s, 1 H), 8.01-7.92 (m, 1 H), 7.80 (dt, J=1.6, 7.8 Hz, 1 H), 7.59 (d, J=7.6 Hz, 1 H), 7.50 (dt, J=1.0, 7.7 Hz, 1 H), 7.23-7.05 (m, 2 H), 6.47 (d, J=8.4 Hz, 1 H), 4.40-4.24 (m, 2 H), 3.83-3.73 (m, 2 H). m/z (ESI) 400.2 (M+H)+.

Provenance & Evidence