Potassium Carbonate → HCID 52935453, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see example 4) (739 mg, 2 mmol), [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (570 mg, 2.60 mmol), potassium carbonate (691 mg, 5.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (146 mg, 0.200 mmol) then filled with 1,4-dioxane (9 mL) and water (3 mL) and purged with nitrogen. The mixture was stirred under microwave irradiation for 30 min at 120° C. then cooled to room temperature. Most of the 1,4-dioxane was removed in vacuo and the residue was partitioned between water and AcOEt. The layers were separated and the aqueous phase extracted twice with AcOEt. The combined organic phases were washed twice with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 25 G silica cartridge (gradient: 13 to 63% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-(4-aminophenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (660 mg, 1.730 mmol, 87% yield) as a pale yellow foam.

Provenance & Evidence