Cesium fluoride → (S)-(3,5-Bis-trifluoromethyl-benzyl)-(4-methyl-3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-(3,5-Bis-trifluoromethyl-benzyl)-(4-bromo-3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (2.16 mmol) in dioxane (150 mL), add bis(diphenylphosphinoferrocene)palladium(II) chloride (0.22 mmol) followed by cesium fluoride (9.32 mmol) and methylboronic acid (6.48 mmol). Heat the mixture under nitrogen to 95° C. After heating for 2 h, cool the reaction mixture to room temperature and dilute with ethyl acetate (50 mL) and water (50 mL). Separate the organics and wash the aqueous with ethyl acetate (2×20 mL). Dry the combined organics over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the crude product over silica gel, eluting with ethyl acetate/hexane (10-45%) to obtain the title compound as an off white solid. MS (ES+): 527 (M+H).

Provenance & Evidence