Hydrochloric Acid → HCID 68328688, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with methyl 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.300 g, 0.658 mmol), 5-methoxy-3-pyridineboronic acid pinacol ester (0.216 g, 0.921 mmol, Sigma-Aldrich), and K3PO4 (0.419 g, 1.973 mmol) in 70% i-PrOH in H2O (3.30 mL). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 10 min. 2 M HCl (aq.) was added and the mixture was extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (eluting with 0-10% MeOH in DCM) to provide methyl 3-(5-methoxy-3-pyridinyl)-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.170 g, 0.389 mmol, 59.1%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 438.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 2.37 (3H, s), 3.96 (3H, s), 4.00 (3H, s), 7.29 (2H, d, J=8.22 Hz), 7.79-7.85 (2H, m), 8.16-8.21 (2H, m), 8.27-8.34 (2H, m), 8.42 (1H, d, J=8.61 Hz), 8.81 (1H, d, J=1.56 Hz).

Provenance & Evidence