Hydrochloric Acid → HCID 178422233, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 6 (0.45 g, 1.78 mmol) in anhydrous DMF (10 mL) was added NaSMe (0.37 g, 5.35 mmol) under N2. The reaction mixture was stirred at 80° C. for 45 min. After cooling, the mixture was poured into a saturated solution of NH4Cl (20 mL), and 1 N HCl (3-4 mL) was added until pH 4-5. The resultant mixture was extracted with EtOAc (5×30 mL), the combined organic extracts were washed with H2O (2×10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was chromatographed on a silica gel column using 5% methanol in CH2Cl2 as eluent to give 7 as an amorphous white solid. Yield: 0.30 g, 70%; ESI MS: m/z 238.9 (M+1).

Provenance & Evidence