Dichloromethane → 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Into a 50 ml round bottom pressure tube were added 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (2.36 g, 5.2 mmol), 2-methoxyphenyl boronic acid (792 mg, 5.2 mmol), [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-complex with dichlormethane (1:1) (43 mg, 0.052 mmol), acetonitrile (20 mL), tetrahydrofuran (5 ml) and of sodium carbonate (aq. 2 M, 9 ml, 18.0 mmol). The flask was sealed and heated at 65° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to give 1.58 g (70%) of 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine. 1H-NMR (250 MHz, CDCl3) δ 8.355 (d, J=2.0 Hz, 1H), 8.155 (d, J=2 Hz, 1H), 7.64 (s, 1H), 7.50 (dd, J=7.5, 1.5 Hz, 1H), 7.23-7.35 (m, 1H), 6.98-7.10 (m, 2H), 5.68 (s, 2H), 3.86 (s, 3H), 3.58 (t, J=8.4 Hz, 2H), 0.94 (t, J=8.4 Hz, 3H), −0.06 (s, 9H); MS: m/z 432.1+434.1 (M+H+).

Provenance & Evidence