Water → HCID 68291682, compound

Participants

Reaction Steps

A mixture of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 5 g, 18.21 mmol), ethanethiol (1.482 mL, 20.04 mmol) and potassium carbonate (5.03 g, 36.4 mmol) in NMP (volume: 60 mL) was stirred at rt for 18 hr. Water (500 ml) was added and the resulting suspension was stirred at rt for 1 hr. The suspension was filtered and the filter cake was air dried. The solid obtained was then washed with hexane and dried to afford a dark yellow solid. This solid was dissolved in warm EtOAc (200 ml) and decolorizing carbon was added. The mixture was allowed to stand for 10 minutes. The mixture was filtered through celite and the filter cake was washed thoroughly with warm EtOAc. The filtrate was concentrated and dried under high vacuum to afford the title compound (3.56 g, 11.86 mmol, 65.1% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (t, J=7.5 Hz, 3 H) 3.11 (q, J=7.4 Hz, 2 H) 5.98 (brs, 1 H) 7.03 (d, J=1.8 Hz, 1 H) 7.83 (d, J=1.8 Hz, 1 H) 7.95 (brs, 1 H) 8.66 (s, 1 H). LCMS (M+H)=299.95/301.95.

Provenance & Evidence