1,2,3,4-Tetrahydroquinoline → HCID 67332018, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of the title compound of Example 3, Step A (50 mg, 0.1 mmol), 1,2,3,4-tetrahydroquinoline (0.019 mL, 0.15 mmol), 2-(di-tert-butylphosphino)biphenyl (1 mg, 0.003 mmol), palladium (II) acetate (0.5 mg, 0.002 mmol) and sodium tert-butoxide (13 mg, 0.14 mmol) was added 0.30 mL of toluene. The reaction was stirred at 90° C. for 16 h, then partitioned between EtOAc/brine acidified with a few drops of 2 N HCl. The aqueous layer was washed with EtOAc then DCM. The combined organic layers were concentrated under reduced pressure to provide the product as a mixture of the title methyl ester and the hydrolyzed carboxylic acid. LC-MS (ESI): m/z=494.3 [M+1]+.

Provenance & Evidence