Dimethylamine → HCID 22638755, compound

Participants

Reaction Steps

A solution of trans-2-[5,6-difluoro-1-(p-toluenesulfonyl)indol-3-yl]cyclopropane-carboxaldehyde (0.48 g, 1.28 mmol), dimethylamine (3 ml, 6 mmol, 2M/THF) and tetrahydrofuran (15 ml) was treated with sodium triacetoxyborohydride (1.35 g, 6.39 mmol) and stirred at ambient temperature for 1 h. The resulting solution was evaporated in vacuo and the residue treated with 10 N sodium hydroxide (10 ml) and methyl alcohol (10 ml). The solution was heated at a gentle reflux for 2 h then cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 1 N sodium hydroxide, and brine, and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to an amber colored oil. Silica gel column chromatography (chloroform/2M ammonia in methanol, 9:1) afforded [2-(5,6-difluoro-1H-indol-3-yl)-cyclopropylmethyl]-dimethyl-amine (100 mg, 31%) as a light oil which solidified upon standing. 1H-NMR (400 MHz, CDCl3) 8.09 (1H, br s), 7.40 (1H, m), 7.10 (1H, dd, J=10.6, 6.6), 6.89 (1H, d, J=2.2 Hz), 2.38 (2H, m), 2.34 (6H, s), 1.69 (1H, m), 1.18 (1H, m), 0.90 (1H, m), 0.78 (1H, m).

Provenance & Evidence