Cesium carbonate → 6-[(2-{[(3R)-3-Hydroxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methyl benzo[b]thiophene-3-carboxylic acid cyclopropylamide

Participants

Reaction Steps

This material was prepared by the reaction of 7-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4a (113 mg, 0.40 mmole) with 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamide 8c (119 mg, 0.48 mmole) and Cs2CO3 (391 mg, 1.2 mmole) in a manner as previously described for example 1 to give a yellow solid (130 mg, 66%). 1H NMR (DMSO-d6, 300 MHz) δ 8.58 (1H, d, J=5.46 Hz), 8.46 (1H, d, J=4.33 Hz), 8.06, 8.00 (1H, s), 7.96 (1H, d, J=2.26 Hz, 7.80 (1H, d, J=8.85 Hz), 7.33 (1H, dd, J=2.35, 8.76 Hz), 6.75 (1H, d, J=5.27 Hz), 5.07 (1H, m), 4.38, 4.33 (1H, br s), 4.02–3.92 (2H, m), 3.67–3.44 (2H, m), 2.93–2.87 (1H, m), 2.57 (3H, s), 2.08–1.79 (2H, m), 0.76–0.70 (2H, m), 0.60–0.55 (2H, m).

Provenance & Evidence