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0 °C

(1R,4R)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol (4-3) (600 mg, 2.6 mmol, 1 eq) was dissolved in DCM (120 mL). The mixture was cooled to 0° C. and DAST (1.6 mL, 12.0 mmol, 4.7 eq) was added. The resulting mixture was stirred at the same temperature for 1 hour. Upon disappearance of starting material, the reaction mixture was poured over NaHCO3 (30 mL) and extracted with CHCl3 (3×50 mL). The combined organics were dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (0-100% Acetone in DCM) to afford 7-fluoro-1-((1R,4S)-4-fluorocyclopent-2-enyl)-1H-imidazo[4,5-c]pyridin-4-amine (4-5) as a white solid. LRMS m/z (M+H) 236.9.0 found, 237.1 required.

1. extractionextracted with CHCl3 (3×50 mL)
2. dry with materialThe combined organics were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe crude residue was purified by flash chromatography (0-100% Acetone in DCM)