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ChemicalBook CAS DataBase List 2-ETHYNYL-BENZO[D]THIAZOLE
40176-80-5

2-ETHYNYL-BENZO[D]THIAZOLE synthesis

3synthesis methods
-

Yield:40176-80-5 120 mg

Reaction Conditions:

with silica gel

Steps:

2-ethynylbenzo[d]thiazole (9)

To a mixture solution of 7 (0.87g, 3.33mmol), and trimethylsilylazide 10a (0.65g, 6.66mmol) in triethylamine (3.3ml) and DCM (7ml) was added Pd(PPh)2Cl2 (47mg) and CuI (14mg), and stirred at 65°C for 4h. The reaction solution was diluted with EtOAc, and filtered. The filtrate was concentrated and purified by silica gel column to give 120 mg of solid 9 (yield 22.6%). Rf: 0.45 (hexane/ethyl acetate=6/1). MS (ESI) m/z 160(M++H), 1HNMR (CDCl3, 300MHz) δ 8.11 (1H, d, J=7.8Hz), 7.89 (1H, dd, J1=7.8Hz, J2=1.5Hz), 7.59~7.40 (2H, m), 3.61(1H, s).

References:

Qi, Jianjun;Tung, Ching-Hsuan [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 1,p. 320 - 323] Location in patent:supporting information; experimental part