Water → HCID 68162631, compound

Participants

Reaction Conditions

Reaction Steps

(2S,4R)-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (for a preparation see intermediate 57) (1.219 g, 3.81 mmol) and 1,1-dimethylethyl methyl{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}carbamate (for a preparation see intermediate 56) (1.608 g, 4.58 mmol) were combined in 1,4-dioxane (15 mL) and water (5.00 mL) under nitrogen to give a clear yellow solution. Potassium carbonate (1.212 g, 8.77 mmol) then [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.419 g, 0.572 mmol) were added and the resulting red mixture was stirred at 110° C. for 16 h then was cooled to room temperature and concentrated in vacuovacuo. The brown residue was suspended in DCM (20 mL) and filtered through a pad of celite (2 g). The insoluble material was washed with DCM (30 mL) and the combined filtrate and washings were concentrated in vacuovacuo. Purification of the residue on SP4 using a 10 G silica cartridge (gradient:1 to 10% MeOH in DCM) gave 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 (1.195 g, 2.66 mmol, 69.6% yield) as a brown foam.

Provenance & Evidence