Binap, (A+-)- → HCID 67207541, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,4R)-1-acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 66) (150 mg, 0.397 mmol) in toluene (4 mL) was treated under nitrogen with 2-chloro-5-Fluoropyridine (63 mg, 0.479 mmol), sodium tert-butoxide (46 mg, 0.479 mmol), racemic BINAP (12.9 mg, 0.021 mmol) and tris(dibenzylideneacetone)dipalladium(0) (19 mg, 0.021 mmol) and the resulting mixture was stirred under nitrogen at 110° C. for 16 h then cooled to room temperature. The mixture was loaded on a 5 g SCX cartridge and eluted with MeOH (25 mL) then with a 2N NH3 in MeOH (25 mL). The ammonia fractions were combined and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel using a 20 G silica cartridge (gradient:1 to 5% (2N NH3 in MeOH) in DCM) gave (2S,4R)-1-acetyl-N-(5-fluoro-2-pyridinyl)-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (49.7 mg, 0.098 mmol, 25%) as an orange oil.

Provenance & Evidence