Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1) → 2-Hydroxy-N-[2-(methylsulfonyl)ethyl]-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-5-carboxamide hydrochloride

Participants

Reaction Steps

Starting materials: methyl 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-5-carboxylate and 2-aminoethylmethylsulfone hydrochloride, but the reaction mixture was after cooling diluted with a saturated sodium hydrogen carbonate solution (10 mL) and concentrated in vacuo. The residue was suspended in methanol/dichloromethane (1:1) and silica gel (˜2 g) was added. The mixture was re-concentrated in vacuo, resulting in a fine yellow powder that was purified on a silica gel column using dichloromethane/methanol/aqueous NH3, (100:10:1), as the eluent to afford the title compound as a base in 36% yield: 1H NMR (DMSO-d6, 300 MHz) δ 14.70 (br s, 1H), 11.42 (br s, 1H), 10.71 (s, 1H), 8.73 (br s, 1H), 8.22 (s, 1H), 8.06 (d, J=9.3 Hz, 1H), 7.99 (s, 1H), 7.82 (d, J=9.3 Hz, 1H), 7.52 (d, J=8.2 Hz, 1H), 6.94 (d, J=8.2 Hz, 1H), 4.25 (s, 2H), 3.98-3.92 (m, 2H), 3.85-3.67 (m, 4H), 3.44-3.29 (m, 4H), 3.12-3.00 (m, 5H); MS (ES) m/z 459 (M++1). The base was converted to the hydrochloride.

Provenance & Evidence