Cesium carbonate → 2-(6'-methoxy-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinoline]-1'-yl)benzo[d]thiazole

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Reaction Conditions

Reaction Steps

A mixture was made of N-(2-bromophenyl)-6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-carbothioamide (200 mg), Cs2CO3 (176 mg), copper iodide (8.5 mg) 1,10-phenanthioline (16.2 mg) and 2 mL 1,2 dimethoxylethane. The mixture was then heated up in a 90° C. oil bath for 1 hour, filtered and evaporated. The residue was passed through a silica gel column (hexane:dichloromethane=10:1), 2-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)benzo[d]thiazole (150 mg) was obtained. 1H-NMR (300 MHz, CDCl3) δ=7.86-6.58 (d, J=8.1 Hz, 1H); 6.58-6.44 (m, 1H); 7.41-7.19 (m, 1H); 7.17-6.96 (m, 1H); 6.64 (s, 1H); 3.87 (s, 3H); 2.76 (s, 2H); 2.18 (s, 3H); 2.17 (s, 3H); 1.96-1.52 (m, 6H) ppm.

Provenance & Evidence