2-Chloropyridine → HCID 68162252, compound

Participants

Reaction Conditions

Reaction Steps

(cis)-1-Acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 25) (100 mg, 0.265 mmol), racemic BINAP (8.25 mg, 0.013 mmol), sodium tert-butoxide (30.5 mg, 0.318 mmol), 2-chloropyridine (0.025 ml, 0.265 mmol) and tris(dibenzylideneacetone)dipalladium(0) (12.13 mg, 0.013 mmol) were suspended in toluene (2.5 mL) under nitrogen and the resulting mixture was stirred at 100° C. for 5 h under microwave irradiation then cooled to room temperature and partitioned between AcOEt (20 mL) and 1:1 saturated NaHCO3 aqueous solution:water (5 mL). The layers were separated and the organic phase washed with saturated NaHCO3 aqueous solution:water (5 mL) then brine (5 mL), dried over Na2SO4 and concentrated in vacuo. Purification of the residue by MDAP (modifier: formic acid) gave (cis)-1-acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-N-2-pyridinyl-1,2,3,4-tetrahydro-4-quinolinamine formate salt (31.9 mg, 0.062 mmol, 24%) as a white solid.

Provenance & Evidence