Hydrochloric Acid → 4-Iodo-2-([1,2]thiazolo[4,5-c]pyridin-7-yl)furo[2,3-c]pyridin-7-amine

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Reaction Conditions

Reaction Steps

A mixture of {7-[bis(tert-butoxycarbonyl)amino]furo[2,3-c]pyridin-2-yl}boronic acid (82.6 mg, 0.219 mmol), 7-bromo[1,2]thiazolo[4,5-c]pyridine (47.0 mg, 0.218 mmol), Pd(PPh3)4 (12.6 mg, 0.0109 mmol), and potassium carbonate (90.6 mg, 0.656 mmol) in 4:1 1,4-dioxane:water (2 mL) was heated to 70° C. for 30 min. Aqueous 12 N hydrochloric acid (0.3 mL, 3 mmol) and methanol (6 mL) was added at 70° C., and the solution was stirred for 2 h. The organic solvents were removed in vacuo, and the material was extracted with DCM and saturated aqueous sodium bicarbonate. The organic layer was purified by column chromatography (1 to 3% 7 N ammonia/methanol:DCM). The purified intermediate was treated with NIS (15.0 mg, 0.0667 mmol) in DMF (1 mL), and the mixture was heated to 40° C. for 20 min. The material was extracted with EtOAc, and washed with aqueous 1 M sodium thiosulfate and brine (2×). The organic layer was concentrated in vacuo to afford 15 mg (17%) of the title compound as a yellow solid. MS (ESI): 395.39 [M+H]+; HPLC tR=1.06 min (HPLC: polar—2 min).

Provenance & Evidence