Iodobenzene → HCID 68184859, compound

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl (2-{4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-1H-pyrazol-1-yl}ethyl)methylcarbamate (for a preparation see intermediate 55) (150 mg, 0.351 mmol), iodobenzene (0.078 mL, 0.702 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (27.6 mg, 0.070 mmol), tris(dibenzylideneacetone)dipalladium(0) (32.1 mg, 0.035 mmol) and sodium tert-butoxide (67.4 mg, 0.702 mmol) were dissolved in 1,4-dioxane (4 mL). The resulting mixture was stirred at 100° C. under nitrogen for 20 h, at 120° C. for 16 h then cooled to room temperature and partitioned between DCM and a saturated NaHCO3 aqueous solution. The layers were separated using an hydrophobic frit and the organic phase concentrated in vacuovacuo. Purification of the residue on SP4 using a 10 G silica cartridge (gradient:20 to 100% AcOEt in hexanes) gave 1,1-dimethylethyl (2-{4-[(2S,4R)-1-acetyl-2-methyl-4-(phenylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-pyrazol-1-yl}ethyl)methylcarbamate (104 mg, 0.206 mmol, 58.9% yield) as a yellow oil.

Provenance & Evidence