Thiophenol → 5-Phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A mixture of 5-bromo-7-azaindole (1)(0.5 g, 2.54 mmol; preparation disclosed in WO2004/078757), benzenethiol (274 μL, 2.66 mmol), sodium t-butoxide (488 mg, 5.07 mmol) and Pd(PPh3)4 (235 mg, 0.20 mmol) in EtOH (25 mL) was heated at reflux for 19 h. More benzenethiol (274 μL, 2.66 mmol), sodium t-butoxide (488 mg, 5.07 mmol) and Pd(PPh3)4 (235 mg, 0.20 mmol) were added and reflux continued for a further 24 h. The reaction mixture was filtered, concentrated, and the residue was extracted with CH2Cl2:hexane=1:1 (v/v). The extract was concentrated and purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 2 as a white solid (142 mg, 25%); 1H NMR (400 MHz, CDCl3) δ 6.53 (dd, J=3.5, 2.0 Hz, 1H), 7.10-7.30 (m, 5H), 7.41 (dd, J=5.9, 2.5 Hz, 1H), 8.16 (dd, J=2.0, 0.6 Hz, 1H), 8.48 (d, J=2.0 Hz, 1H), 10.00-10.20 (bs, NH).

Provenance & Evidence