1-Methyl-5-(tri-n-butylstannyl)imidazole → HCID 52934103, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methyl-5-(tributylstannyl)-1H-imidazole (200 mg, 0.54 mmol), 1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (199 mg, 0.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol) in dry, degassed DMF (5 mL) was stirred at 140° C. under nitrogen for 16 h then was cooled to room temperature and diluted with AcOEt (20 mL). The solution was washed with water (×2) then brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(1-methyl-1H-imidazol-5-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (27 mg, 0.073 mmol, 13%) as a colourless solid after trituration with AcOEt/hexane. LCMS (method G): Retention time 0.59 min, [M+H]+=402.1

Provenance & Evidence