Water → HCID 57421974, compound

Participants

Reaction Conditions

Reaction Steps

Aluminum chloride (0.48 g, 3.6 mmol) was added slowly to a stirred solution of 5-fluoro-1H-pyrrolo[2,3-b]pyridine (0.164 g, 1.2 mmol) in CH2Cl2 (5 mL)). Bromoacetyl bromide (0.1 mL, 1.5 mmol) was added and the resulting solution was heated at 50° C. for 1 h and cooled to room temperature. Water (25 mL) was added, the solution was basified with saturated NaHCO3 and the mixture was extracted with EtOAc (3×25 mL). The organic extracts were dried and concentrated under reduced pressure to give 2-bromo-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone as a pale brown solid. A mixture of 2-bromo-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (0.28 g) and thiourea (0.13 g) in ethanol (10 mL) were heated at 70° C. for 1 h. Water (50 mL) was added and the solution was basified with concentrated NH4OH. The aqueous layer was extracted with EtOAc (3×25 mL). The organic extracts were dried and concentrated under reduced pressure to give 4-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)thiazol-2-amine (0.21 g, 75%, 2 steps) as pale brown solid. Mass Spec.; MS 235 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.86(s, 1H), 8.27(d, 1H), 8.22(s,1H), 7.83(d,1H), 6.95(brs,2H), 6.81(s,1H).

Provenance & Evidence