2-Bromo-5-methylpyridine → HCID 68161807, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4R)-1-acetyl-6-[1-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 44) (48 mg, 0.112 mmol) and 2-bromo-5-methylpyridine (57.7 mg, 0.335 mmol) in toluene (2.5 mL) were successively added sodium tert-butoxide (107 mg, 1.117 mmol), tris(dibenzylideneacetone)dipalladium(0) (20.46 mg, 0.022 mmol) and 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (17.59 mg, 0.045 mmol). The reaction mixture was stirred at 75° C. for 5 h then cooled to room temperature, and filtered through Celite. The insoluble material was washed with 5% MeOH in DCM. The combined filtrate and washings were concentrated in vacuo. Purification of the residue on SP4 using a 10 G silica cartridge (gradient:10 to 80% AcOEt in Hexanes) gave (2S,4R)-1-acetyl-6-[1-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-N-(5-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (34 mg, 0.065 mmol, 58%) as a colourless oil.

Provenance & Evidence