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

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, 44 (9.60 g, 35.2 mmol), copper (II) acetate monohydrate (14.05 g, 70.4 mmol), and PdCl2(CH3CN)2 (0.91 g, 3.5 mmol) were placed under a nitrogen atmosphere. Acetonitrile (60 mL) was added followed by methyl acrylate (9.52 mL, 105.6 mmol). The mixture was heated at 110° C. for 20 h, allowed to reach rt, diluted with EtOAc, and washed with water and brine. The combined organic layers were dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 20% EtOAc-hexanes to provide 3.86 g (30%) of product 45 as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.46 (s, 3H), 3.81 (s, 3H), 6.39 (d, J=16 Hz, 1H), 6.97 (s, 1H), 7.06-7.08 (m, 1H), 7.39 (d, J=8 Hz, 1H), 7.40-7.45 (m, 1H), 7.84-7.90 (m, 1H), 7.94-7.96 (m, 1H), 8.06 (dt, J=1, 8 Hz, 1H), 8.42 (d, J=16 Hz, 1H), 8.52-8.54 (m, 1H). LC-MS (CI): m/z 357.1 [(M+H)+ C18H16N2O4S requires 356.08].

Provenance & Evidence