Tetrabutylammonium Fluoride → 2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

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Reaction Steps

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (230 mg, 0.41 mmol) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 3.2 mL) was stirred at 25° C. for 16 h. The mixture was diluted with ethyl acetate (100 mL), washed with a saturated aqueous ammonium chloride solution (4×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[2-cyclopentyl-1-(6-methanesulfonyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (150 mg, 86%) which was used in the next step without further purification: LC/MS m/e calcd for C22H23N3O4S [M+H]+ 426.51, observed 426.2.

Provenance & Evidence