Dimethylformamide → HCID 68185395, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (355 mg, 0.962 mmol) in N,N-dimethylformamide (DMF) (5 mL) at room temperature was degassed over 30 min under house vacuum and quenched several times with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmol) and zinc(II) cyanide (153 mg, 1.3 mmol) were then added and the resulting yellow mixture was stirred under nitrogen at 100° C. for 5 h then cooled to room temperature. The insoluble were filtered off, rinsed with AcOEt then destroyed with bleach. The organic phase was washed with water. The aqueous phase was extracted with AcOEt. The combined organic phases were washed twice with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 10 G silica cartridge (gradient: 13 to 63% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-cyano-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (238 mg, 0.755 mmol, 78% yield) as a white solid.

Provenance & Evidence