Dimethylformamide → HCID 68752316, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tert-butyl 6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (0.44 g, 2.0 mmol, WO2009158394, Example M-In-1) and DMF (10 mL). The mixture was cooled to about 0° C. and NaH (60% dispersion in mineral oil, 0.095 g, 2.4 mmol) was added. The mixture was stirred at about 0° C. for about 20 min followed by the addition of TsCl (0.41 g, 2.2 mmol). The resulting mixture was stirred at about 0° C. for about 90 min and then at about rt for about 3.5 h. The mixture was poured into DCM (40 mL) and water (20 mL) was added. The layers were separated and the organic solution was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in DCM to give tert-butyl 3-tosyl-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (0.21 g, 28%): LC/MS (Table 2, Method n) Rt=2.53 min; MS m/z: 378 (M+H)+.

Provenance & Evidence