Allyl bromide → methyl 2-[2-(allyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate (prepared as described in published International patent application WO 2006/046030) was suspended in MeCN/DCM (1:1, 0.1M) and K2CO3 (1 eq) was added. To the stirred mixture allyl bromide (1.1 eq) was added and the mixture was warmed to 50° C. After 4 h a further 0.5 eq of allyl bromide were added and heating was continued over night. The mixture was filtered and the filter cake was extracted with hot ethyl acetate. The combined filtrates were evaporated in vacuo. The residual material was dissolved in hot DCM and precipitated by addition of PE. The precipitate was collected and dried in vacuo. The product was obtained as a beige crystalline powder. (81%). (ES+) m/z 390 (M+H)+.

Provenance & Evidence