2-Amino-5-bromo-N,N-dimethylbenzamide → 2-amino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g, 3 mmol), 2-amino-5-bromo-N,N-dimethyl-benzamide 0.8, 3.3 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (110 mg, 0.2 mmol) in THF/Acetonitrile/saturated NaHCO3 (5 ml/5 ml/5 ml) was stirred at 100° C. for 4 hours. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (3×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2-amino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (1.1 g, 71% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.29 (s, 3H), 2.89 (s, 6H), 3.77 (s, 3H), 6.74 (d, 1H), 7.03 (m, 1H), 7.14 (d, 1H), 7.29 (s, 1H), 7.34-7.41 (m, 4H), 7.55 (d, 1H), 7.94 (s, 2H), 8.01 (d, 2H), 8.54 (s, 1H). MS: m/z 541.1 (M+H+).

Provenance & Evidence