4-Hydroxymethylpyridine → ethyl 6-trimethylsilyl-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

0.42 g (3.82 mmol) of 4-pyridinylmethanol and 0.92 g (3.826 mmol) of (cyano-methylene)tributylphosphorane (CMBP) are added, at ambient temperature, to a solution of 0.5 g (1.91 mmol) of ethyl 6-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 1.2, in 8 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is stirred at 110° C. for 15 hours and then concentrated to dryness. The reaction crude is subsequently purified by flash chromatography on a silica gel column, elution being carried out with a mixture of heptane and ethyl acetate, to give 0.644 g of the expected ethyl 6-trimethylsilyl-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate in the form of a yellow solid.

Provenance & Evidence