2,6-Dimethylphenol → HCID 56682223, compound

Participants

Reaction Steps

To a solution of 2,6-dimethylphenol (152 mg, 1.24 mmol) in NMP (3 ml) was added sodium hydride (50 mg, 1.24 mmol, 60% dispersion in mineral oil), and the suspension was stirred at room temperature under an argon atmosphere for 20 min. After addition of 100 mg (207 μmol) of the compound of step 7, the reaction mixture was stirred for 2 h at 140° C. After cooling, the reaction mixture was quenched with water and extracted with EA. The organic phases were concentrated and the remaining residue was dissolved in DCM (12 ml) and TFA (3 ml) and stirred at room temperature for 2 h. The solvents were evaporated and the resulting solid was purified by preparative HPLC. The fractions containing the title compound were combined and lyophilized overnight. The obtained solid was dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight to give 34 mg of the title compound in the form of the [2-(2,6-dimethyl-phenoxy)-1-phenyl-4-propyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochloride.

Provenance & Evidence