Dimethylformamide → HCID 18617606, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.46 mL (15.7 mmol) phosphorous oxychloride in 5 mL DMF is stirred for 20 minutes. A solution of 2.11 g (13.1 mmol) 5-(2-hydroxyethyl)indole (reference example 6) in 5 mL DMF is added, and the reaction mixture is heated to 80° C. for ten minutes. The reaction is quenched with solid sodium bicarbonate and diluted with 250 mL 1:1 CH2Cl2:MeOH. The inorganic solids are filtered off, and the filtrate concentrated. The resulting residue is refluxed in 75 mL 1N HCl solution for one hour, then extracted with CH2Cl2. The organic extracts are combined and concentrated, and the residue chromatographed (20:1 CH2Cl2:MeOH) to provide 2.45 g of the product as a brown solid in 90% yield. 1H NMR (CDCl3): δ 3.19 (2H, t, J=7 Hz), 3.76 (2H, t, J=7 Hz), 7.20 (1H, dd, J=8, 1 Hz), 7.40 (1H, d, J=8 Hz), 7.85 (1H, d, J=3 Hz), 8.19 (1H, s), 8.98 (1H, br), 10.05 (1H, s). MS (EI) m/z 207, 209 (M[35Cl, 37Cl])+, 158 (M−CH2Cl)+.

Provenance & Evidence