2-Bromopyridine → HCID 52936220, 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) (100 mg, 0.233 mmol) and 2-bromo pyridine (110 mg, 0.698 mmol) in toluene (2.5 mL) were successively added sodium tert-butoxide (224 mg, 2.328 mmol), tris(dibenzylideneacetone)dipalladium(0) (213 mg, 0.233 mmol) and 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (183 mg, 0.466 mmol). The resulting mixture was stirred at 100° C. for 2 h then cooled to room temperature and filtered through Celite. The insoluble material was washed with 5% MeOH in DCM and the combined filtrate and washings were concentrated in vacuo. The residue was dissolved in a 1:1 MeOH/DMSO mixture and purified via MDAP (modifier: formic acid). The appropriate fractions were combined and concentrated using a blow down apparatus (45° C.) to give 2-{4-[(2S,4R)-1-acetyl-2-methyl-4-(2-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}ethanol as a colourless oil.

Provenance & Evidence