Potassium Carbonate → 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (50 mg, 0.123 mmol), 4-methoxyphenylboronic acid (37.4 mg, 0.246 mmol), K2CO3 (42.5 mg, 0.308 mmol), and PdCl2(dppf)-CH2C12 adduct (10.05 mg, 0.012 mmol) in dioxane (3 mL) was sealed in a microwave vial and it was heated in an oil-bath at 120° C. for 16 h. The reaction mixture was concentrated and the crude was purified by preparative HPLC to give 18 mg of 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as light brown solid. MS (ESI) m/z 434.2 (M+H). 1H NMR (methanol-d4) d ppm 7.64-7.73 (m, 2H) 7.52 (d, J=8.8 Hz, 2H) 6.89 (d, J=8.8 Hz, 2H) 3.73 (s, 3H) 3.52-3.67 (m, 8H) 3.00-3.12 (m, 1H) 2.70-2.89 (m, 4H) 1.83-2.09 (m, 2H).

Provenance & Evidence