Ethanol → HCID 52934794, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (108 mg, 0.259 mmol), 2-chloropyridine (35.3 mg, 0.311 mmol), potassium carbonate (108 mg, 0.778 mmol) and tetrakis(triphenylphosphine)palladium(0) (14.99 mg, 0.013 mmol) in ethanol (2.5 mL) and toluene (2.5 mL) was degassed for 15 min under house vacuum and quenched several times with nitrogen, and then was heated at 100° C. for 1 h before being cooled to room temperature and partitioned between AcOEt (30 mL) and water (15 mL). The layers were separated and the aqueous phase was extracted with AcOEt (15 mL). The combined organic phases were washed with brine (15 mL), dried over MgSO4 and concentrated in vacuo. Purification of the residue by MDAP (reversed phase, water/acetonitrile, modifier: ammonium bicarbonate) gave 1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-(2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (32.1 mg, 0.087 mmol, 34%) as a white solid.

Provenance & Evidence