Sodium Carbonate → 1-Benzenesulfonyl-5-bromo-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A mixture of 46 (1 g, 2.16 mmol), EtOH (14 mL), toluene (14 mL), 1-trityl-1H-pyrazole-4-boronic acid (767 mg, 2.16 mmol), 1M aq. Na2CO3 (5.4 mL, 5.4 mmol), LiCl (275 mg, 6.5 mmol) and PdCl2(PPh3)2 (75 mg, 0.108 mmol) was refluxed for 1 h 45 min. The reaction mixture was concentrated to afford a pale yellow solid. The solid was purified by silicagel chromatography (Si 50 g column) using 30% ethyl acetate in hexane as eluent (gradient elution) to give the product 47 (798 mg, 57%) as a pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 7.18-7.23 (m, 6H), 7.33-7.37 (m, 9H), 7.47 (t, J=15.6, 7.4 Hz, 2H), 7.57-7.60 (m, 2H), 7.74 (s, 1H), 7.91 (s, 1H), 7.95 (d, J=2.1 Hz, 1H), 8.15-8.18 (m, 2H), 8.46 (d, J=2.2 Hz, 1H).

Provenance & Evidence