Potassium Phosphate, Tribasic → HCID 86711854, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyl-4-bromo-3-(4-chlorophenyl)-N-(2,2-dimethylpropyl)-N-methyl-5-(trifluoromethyl)pyrrole-2-carboxamide (100 mg, 0.18 mmol) in Toluene (1 mL) was added cyclopropylboronic acid (2 equiv., 0.032 g, 0.37 mmol), Palladium(II) acetate (0.1 equiv., 0.004 g, 0.018 mmol), 2-(DICYCLOHEXYLPHOSPHINO)-2′,4′,6′-TRI-I-PROPYL-1,1′-BIPHENYL (0.2 equiv., 0.01796 g, 0.03691 mmol) and POTASSIUM PHOSPHATE TRIBASIC (3 equiv., 0.1212 g, 0.04726 mL, 0.5537 mmol) in a Reactivial. The reaction was heated to 120° C. overnight. Work up: Reaction mixture cooled to room temperature and diluted with Ethyl Acetate. Filtered through celite and celite washed, through 3× Ethyl Acetate. Organics reduced under vacuum to residue. Purification: Purified via 25 g Silica Column using 0-100% Petrol Ether/(10% Ethyl Acetate/Petrol Ether) over 30 minutes collecting at 254 nm. Major peak isolated and reduced under vacuum to yield ˜90 mg (45%) white foam. Purified further via preparative HPLC using 70-95% acetonitrile/water (0.1% formic acid) over 20 min collecting at 254 nm. Pure fractions combined and reduced under vacuum.

Provenance & Evidence