Cesium carbonate → HCID 86664065, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-(3-chloro-1,2,4-thiadiazol-5-yl)-4-ethylpiperidine-4-carboxylate (110 mg, 0.35 mmol), cesium carbonate (285.6 mg, 0.88 mmol), Pd(dppf)2Cl2 (20 mg, 0.03 mmol) and {2-[(ethylcarbamoyl)amino]-7-(pyridin-2-yl)-1,3-benzothiazol-5-yl}boronic acid (100 mg, 0.29 mmol) was suspended in a mixture of THF (9 mL) and water (1 mL) and heated in the microwave at 110° C. for 50 min. The reaction mixture was concentrated in vacuo and the residue partitioned between 10% IPA/DCM (10 mL) and water (10 mL). The organic layer was separated and the aqueous extracted with further 10% IPA/DCM (3×10 mL), the organic layers were combined, dried (MgSO4), filtered and concentrated to give a black solid which was pre-absorbed onto silica and purified by flash column chromatography (Biotage SP4 12 g, 2% MeOH/DCM-5% MeOH/DCM-8% MeOH/DCM) to give the desired product as a brown solid. MS: 566.11 [M+H]+.

Provenance & Evidence