Acetic Acid → HCID 66604576, compound

Participants

Reaction Conditions

Reaction Steps

A 5-ml microwave vial was loaded with 5-benzyl-2-(4-(morpholine-4-carbonyl)phenylamino)benzonitrile (42 mg, 0.080 mmol), acetic acid (4 mL) and palladium acetate (45.1 mg, 0.201 mmol). The flask was sealed and heated to 130° C. for 13 hours. The reaction mixture was filtered through a 0.45 um Nylon filter and concentrated in vacuum. The crude was filtered through a layer of BIOTAGE® Si-propylthiol resin (0.8 g in a 6 ml cartridge, to remove Pd) and rinsed with methanol. The pale yellow eluent was concentrated and purified by prep HPLC to give 7.0 mg 3-benzyl-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/e−412, m/e+=414 consistent with [M−H]− and [M+H]+ resp. HPLC retention time 9.14 min. (Sunfire C18 3.5 μm, 4.6×150 mm column, 15 min gradient, 10-100% B, 1 mL/min. Solvent A: 5% CH3CN—95% H2O—0.1% TFA; Solvent B: 95% CH3CN—5% H2O—0.1% TFA). 1H NMR (CD3OD) δ ppm 8.18 (m, 2H), 7.87 (s, 1H), 7.65 (b, 1H), 7.52 (b, 1H), 7.30 (m, 4H), 7.20 (b, 1H), 4.21 (s, 2H), 3.90-3.50 (b, 8H).

Provenance & Evidence