Sodium Carbonate → 2-(1H-indol-5-yl)-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide (60 mg, 0.149 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (72.3 mg, 0.298 mmol), Potassium phosphate tribasic (134 mg, 0.476 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (24.43 mg, 0.060 mmol) and Pd(OAc)2 (6.68 mg, 0.030 mmol) were mixed with THF (2 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 85° C. in an oil bath for 3.5 hr. LC/MS showed there was trace amount of product formed. The reaction mixture was blown to dryness under N2 blower. To the mixture was added Pd(Ph3P)4 (34.4 mg, 0.030 mmol), Toluene (3 mL), MeOH (1.5 mL) and Na2CO3 (2M) (0.149 mL, 0.298 mmol). The mixture was then heated at 100° C. for 3 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 440.3 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.65 (s, 1H), 11.20 (s, 1H), 8.67 (s, 1H), 8.5 (m, 2H), 8.32 (d, 1H, J=8.2), 8.12 (d, 1H, J=8.5), 7.9 (s, 1H), 7.8 (s, 1H), 7.53(d, 1H, J=8.0), 7.41(m, 1H), 7.30 (d, 1H, J=8.0), 6.57 (s, 1H), 3.66 (bs, 8H).

Provenance & Evidence