Cesium carbonate → 6-(2-[3-Methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzofuran-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 (144 mg, 0.5 mmole) with 6-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid methylamide 11c (120 mg, 0.6 mmole) and Cs2CO3 (794 mg, 2.4 mmole) in a manner as previously described for example 1 to give 134 mg (59%) of an off-white solid. 1H NMR (DMSO-d6) δ 8.58 (1H, d, J=5.3 Hz), 8.07 (1H, s), 7.97 (1H, d, J=4.5 Hz), 7.83 (1H, d, J=8.6 Hz), 7.65 (1H, d, J=2.0 Hz), 7.24 (1H, dd, J=2.0, 8.6 Hz), 6.72 (1H, d, J=5.3 Hz), 4.25–3.75 (3H, m), 3.65–3.45 (2H, m), 3.27, 3.24 (3H, s), 2.82 (3H, d, J=4.3 Hz), 2.62 (3H, s), 2.15–1.95 (2H, m). Anal. Calcd for C24H23N3O5S.0.5H2O: C, 60.74; H, 5.10; N, 8.86; S, 6.76. Found: C, 60.89; H, 5.16; N, 8.69; S, 6.58.

Provenance & Evidence