Acetic Anhydride → HCID 178467166, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-6-phenyl-4-piperidylpyrrolo[3,2-d]pyridine (Example 35) (50 mg, 0.17 mmol), acetic anhydride (Aldrich Chemical Company) (168 mg, 1.64 mmol, 9.7 eq), K2CO3 (227 mg, 1.64 mmol, 9.7 eq) and 4—N,N-dimethylaminopyridine (2.6 mg, 0.021 mmol, 0.12 eq) in anhydrous DMF (2.0 mL) was stirred under N2 at 110° C. overnight. After cooling to the room temperature, the reaction was quenched by the addition of saturated NaHCO3 (5 mL) and extracted with CHCl3 (3×30 mL). The organic layers were washed with saturated NaCl, dried over Na2SO4 and concentrated with a rotary evaporator. The crude material was purified by flash chromatography on silica gel with a gradient eluant of EtOAc(0-25%):hexanes(100-75%) to afford 13 mg (22%) of the title compound as an off-white solid. Mp: 188-190° C. 1H NMR (CDCl3; 400 MHz): δ 11.43 (s, 1), 7.61 (d, 2, J=7.4), 7.43 (t, 2, J=7.4), 7.37 (t, 1, J=7.4), 4.88 (br s, 2), 4.06 (br s, 2), 2.58 (s, 3), 2.11 (s, 3), 1.73 (br s, 6). MS m/z: 335 (M+1), 333 (M−1). HRMS (NBA-NaI) m/z Calcd for M+H, C20H22N4O: 335.1888. Found: 335.1872.

Provenance & Evidence