Methyl 3-(6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indol-2-yl)acrylate → methyl 3-(6-methyl-1H-indol-2-yl)propanoate

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Reaction Conditions

Reaction Steps

A suspension of 45 (1.86 g, 5.22 mmol) and Mg (2.54 g, 104.4 mmol) in MeOH (40 mL) was stirred at 0° C. for 2 h. The mixture was diluted with EtOAc and filtered through a pad of Celite. The filtrate was washed with a sat. NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 10% EtOAc-hexanes to provide 0.69 g (60%) of product 46 as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.43 (s, 3H), 2.74 (t, J=7 Hz, 2H), 3.06 (t, J=7 Hz, 2H), 3.71 (s, 3H), 6.17 (m, 1H), 6.90 (d, J=8 Hz, 1H), 7.10 (s, 1H), 7.40 (d, J=8 Hz, 1H), 8.36 (brs, 1H). LC-MS (CI): m/z 218.1 [(M+H)+ C13H15NO2 requires 217.11].

Provenance & Evidence