Toluene → HCID 68185438, compound

Participants

Reaction Conditions

Reaction Steps

1-Methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1 g, 2.71 mmol) (for a preparation see Example 4) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine (0.487 g, 2.213 mmol) were combined in ethanol (4.7 ml) and toluene (4.70 ml) to give a light yellow solution. K2CO3 (0.449 g, 3.25 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (0.156 g, 0.135 mmol) were added and the resulted mixture was stirred at 90° C. under nitrogen for 16 h then was cooled to room temperature and concentrated in vacuo. The residue was partitioned between water (40 mL) and EtOAc (50 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (50 mL) and the combined organic phases were washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 12 to 63% AcOEt in Hexanes followed by 10% (2M NH3 in MeOH) in DCM) gave a residue which was further purified by flash chromatography on silica gel (gradient: 1 to 5% (2M NH3 in MeOH) in DCM) to give 1-methylethyl[(2S,4R)-1-acetyl-6-(6-amino-3-pyridinyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (0.74 g, 1.885 mmol, 69.6% yield) as a yellow foam.

Provenance & Evidence