Cesium carbonate → HCID 24803745, compound

Participants

Reaction Steps

Add Cs2CO3 (339 mg, 1.04 mmol) to a slurry of 2-(4-chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-6H-thieno[2,3-c]pyridin-7-one, (Preparation 47) (200 mg, 0.522 mmol), in 10 mL CH3CN (10 mL). Stir 1 h and then add toluene-4-sulfonic acid (S)-4-methyl-5-oxo-morpholin-3-ylmethyl ester (172 mg, 0.57 mmol). Warm to reflux overnight. Cool to RT, pour into 1 M NaOH (100 mL) and extract with CH2Cl2 (3×100 mL). Wash the combined organic extracts with brine (100 mL). Purify via silica gel chromatography using 0-5-20% (2 N NH3 in MeOH)/CHCl3 to give 41 mg of product that is 86% pure. Recrystallize from CH2Cl2/hexanes to give 28 mg of the desired product in good purity. MS/ES m/z (35Cl) 511.0 [M+H]+.

Provenance & Evidence