Tetrahydrofuran → HCID 49793320, compound

Participants

Reaction Conditions

Reaction Steps

2.93 g (9 mmol) of caesium carbonate are dried in an evacuated Schlenk flask under temperature, and 50 ml of dry tetrahydrofuran, 978 mg (3.00 mmol) of tert-butyl N-(5-iodo-1,3-thiazol-4-yl)carbamate, 396 mg (3.30 mmol) of 1-ethynyl-4-fluorobenzene, 122 mg (0.15 mmol) of Pd(dppf)2Cl2.CH2Cl2 and 57 mg (0.30 mmol) of CuI are subsequently added under nitrogen. The reaction mixture is heated at 50° C. for 6 h, subsequently cooled and filtered through Celite, and the solvent is removed in vacuo. The residue is taken up with ethyl acetate and washed with saturated NaCl solution. The combined organic phases are dried over sodium sulfate, evaporated in vacuo, and the residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1), giving 820 mg (2.57 mmol, 85%) of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate as yellow solid from diethyl ether;

Provenance & Evidence