Cesium carbonate → 1,2-dimethyl-6-(2-[3-methoxy-pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-1H-indole-3-carboxylic acid methylamide

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Reaction Steps

This material was prepared by the reaction of 7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4b (157 mg, 0.5 mmole) with 6-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid methylamide 16e (150 mg, 0.7 mmole) and Cs2CO3 (673 mg, 2.1 mmole) in a manner as previously described for example 1 to give 51 mg (39%) of a crisp foam. 1H NMR (DMSO-d6) δ 8.54 (1H, dd, J=5.5, 1.13 Hz), 8.05 (1H, s), 7.84 (1H, d, J=8.6 Hz, 7.61–7.55 (1H, m), 7.54 (1H, d, J=2.1 Hz), 7.03(1H, dd, J=2.1, 8.6 Hz), 6.64 (1H, d, J=5.5 Hz), 4.12–3.51 (5H, m), 3.67 (3H, s), 3.27, 3.24 (3H, 2s), 2.80 (3H, d, J=4.5 Hz), 2.60 (3H, s), 2.35–1.95 (2H, m). Anal. Calcd for C25H26N4O4S.0.9 H2O0.2 EtOAc: C, 60.47; H, 5.78; N, 10.93; S, 6.26. Found: C, 60.46; H, 5.56; N, 10.81; S, 6.34.

Provenance & Evidence