Dimethylformamide → HCID 86035944, compound

Participants

Reaction Steps

The title compound is prepared following the procedure of Andreani, A. et al., J. Med. Chem. 20, (1977) 1344-1346 as follows. To a mixture of dimethylformamide (0.50 mL) and dichloromethane (0.50 mL) is added phosphorus oxychloride (0.50 mL) at 0° C. After stirring for 15 min, a solution of 1-(pyridin-2-yl)-1,3-dihydroindol-2-one (Le Baunt, G. et al., EP 0 580 502) (250 mg, 1.2 mmol) in dichloromethane (2.0 mL) and pyridine (0.25 mL) is added and the resulting dark-red solution is stirred for 36 hr. The reaction mixture is poured onto ice water and extracted with dichloromethane. The combined organic layer is washed with water, with saturated sodium bicarbonate, with brine, dried over sodium sulfate, filtered and concentrated. The dark residue is purified by chromatography eluting with dichloromethane-0 to 3% methanol. Product containing fractions are combined and concentrated to afford 2-chloro-1-(pyridin-2-yl)-1H-indole-3-carboxaldehyde (70 mg, 23% yield) as a beige solid. TLC (dichloromethane) Rf=0.18; ESI/MS 257 (M+H); RT=2.99 min; NMR 10.16 (1H, s); 8.79 (1H, d); 8.25 (2H, m); 7.84 (1H, d, J=9 Hz); 7.73 (1H, m); 7.40 (3H, m).

Provenance & Evidence