1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)-

1679-18-1

183208-35-7

918516-27-5

General method: Steps: 5-bromo-7-azaindole (2 g, 10.2 mmol, 1.0 eq.), K2CO3 (2.8 g, 20.3 mmol, 2 eq.) and 4-chlorobenzeneboronic acid (1.8 g, 11.2 mmol, 1.1 eq.) were suspended in a solvent mixture of DME/H2O (30 ml, 4:1) and degassed with argon. Pd(PPh3)4 (587 mg, 508 μmol, 0.05 eq.) was added and the reaction mixture was heated to reflux until the feedstock was completely consumed. Upon completion of the reaction, the solution was allowed to filter through a diatomaceous earth pad, diluted with EtOAc and washed with water. The organic layers were combined, dried with Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified by fast chromatography (SiO2, hexane/EtOAc 6:4). Yield: 2.23 g, 9.4 mmol, 92% (white solid).TLC: petroleum ether/EtOAc 1:1.1H NMR (DMSO-d6, 200 MHz, ppm): δ 11.76 (s, 1H), 8.51 (d, J = 2.1 Hz, 1H), 8.20 (d, J = 1.9 Hz, 1H), 7.72 (d, J = 8.5 Hz, 2H), 7.57-7.43 (m, 3H), 6.50 (dd, J=3.2,1.7 Hz, 1H).13C NMR (DMSO-d6, 50 MHz, ppm): δ148.2, 141.4, 138.0, 131.7, 128.9, 128.6, 127.1, 126.9, 126.1 , 117.7, 100.2.