Tributylstannane → HCID 57028617, compound

Participants

Reaction Steps

A solution of tributyltin hydride (0.251 ml, 0.934 mmol) in benzene (10 ml) was added dropwise over 30 minutes to a stirred solution of 1-acetyl-2,3-dihydro-6-iodo-5-[(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)methylthio]-1H-indole (D51) (0.200 g, 0.467 mmol) and AIBN (5 mg) in benzene (20 ml) under argon at reflux. Reflux was continued for a further 0.75 h. The reaction mixture was then allowed to cool. Ethyl acetate (10 ml) was then added and the mixture washed with 2.5M HCl (3×10 ml). The combined aqueous washings were then basified with solid potassium carbonate and the resultant suspension was extracted with dichloromethane (3×15 ml). The combined organic extracts were then dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow solid which was dried in vacuo (0.127 g). The solid was purified by prep. TLC (15% MeOH/CH2Cl2 as eluant) to give the title compound as a cream solid (0.047 g, 33%).

Provenance & Evidence