Allyltributylstannane → tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled into a solution of tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (3.68 g, 9.66 mmol) in DMF (50 mL) for 1 h. Allyltributyltin (3 mL, 9.66 mmol) was added to the reaction mixture followed by the addition of Pd(PPh3)4 (1.1 g, 10 mol %). The reaction was heated at 80° C. for 6 h and then diluted with EtOAc and H2O. The entire solution was filtered over celite and to the solute was added 20% aqueous KH2PO4. The organics were separated and dried over sodium sulfate. After removal of solvent, the crude product was purified by silica gel chromatography to provide tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate (2.52 g, 76%). MS (m/z) 330 [M+H]+.

Provenance & Evidence