2-Bromo-5-methylpyridine → HCID 67206538, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]benzoate (for a preparation, see Intermediate 52) (153 mg, 0.434 mmol) and 2-bromo-5-methylpyridine (224 mg, 1.302 mmol) in toluene (10 mL) were successively added sodium tert-butoxide (417 mg, 4.34 mmol), tris(dibenzylideneacetone)dipalladium(0) (398 mg, 0.434 mmol) and 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (342 mg, 0.868 mmol). The resulting mixture was stirred at 100° C. for 3 h then cooled to room temperature. The insoluble material was washed with 5% MeOH in DCM. The combined filtrate and washings were concentrated in vacuo and the residue was dissolved in a 1:1 MeOH/DMSO mixture and purified via MDAP (modifier: formic acid). The appropriate fractions were combined and the solvents evaporated using a blow down apparatus to give 4-{(2S,4R)-1-acetyl-2-methyl-4-[(5-methyl-2-pyridinyl)amino]-1,2,3,4-tetrahydro-6-quinolinyl}benzoic acid (27.5 mg, 0.066 mmol, 15%) as an off white solid.

Provenance & Evidence