Potassium Phosphate, Tribasic → HCID 67376680, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 3-(3,6-dihydro-2H-pyran-4-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.058 g, 0.165 mmol), potassium acetate (0.032 g, 0.329 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (5.83 mg, 8.23 μmol), and (2-iodo-3-methylphenyl)(pyrrolidin-1-yl)methanone (0.078 g, 0.247 mmol). The vessel was evacuated and flushed with N2 gas 3× before EtOH1 (1.6 mL) and water (0.23 mL) (each degassed by bubbling N2 gas through the solution for 10 min prior to addition) was added. The reaction mixture was stirred and heated in a microwave reactor at 130° C. for 10 min. 2-(Dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.012 g, 0.026 mmol), potassium phosphate tribasic (0.041 mL, 0.494 mmol), Pd2(dba)3 (7.54 mg, 8.23 μmol) were added and the reaction was degassed and heated in the Initiator microwave reactor again for 20 min at 130° C. The reaction mixture was diluted with 10:1 saturated ammonium chloride/ammonium hydroxide and extracted with EtOAc. The combined organic extracts were washed with 10:1 saturated ammonium chloride/ammonium hydroxide, water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was purified by silica gel chromatography by eluting with 1:20 2M NH3 in MeOH/DCM, to provide (2-(2-amino-3-(3,6-dihydro-2H-pyran-4-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone.

Provenance & Evidence