Dimethylformamide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carbonyl chloride

Participants

Reaction Steps

To a solution of Intermediate 28 (2 g; 7.80 mmol) in DCM (40 mL) was added oxalyl chloride (1.98 mL; 23.41 mmol) followed by DMF (60 μL) under vigorous stirring at RT. After 2 h, solvents were removed under vacuum to give 2-(methoxymethyl)-2′-methylbiphenyl-4-carbonyl chloride as a yellow oil that was dried under vacuum. To a solution of Intermediate 62 (150 mg; 0.49 mmol) in CH3CN (1.50 mL) and DI EA (0.33 mL) was added a solution of 2-(methoxymethyl)-2′-methylbiphenyl-4-carbonyl chloride (134.07 mg; 0.49 mmol) in CH3CN (1.50 mL). Reaction mixture was stirred at RT for 1 h 30 after which it was heated to 150° C., 30 min under microwave irradiations. Reaction mixture was concentrated under vacuum, dissolved in DCM and purified by column chromatography (EtOAc:cHex from 10:90 to 80:20) to give the title compound as a colorless oil. LC/MS (Method B): 528.5 (M+H)+.

Provenance & Evidence