Ammonium Chloride → HCID 67148313, compound

Participants

Reaction Conditions

Reaction Steps

To a sol. of 4-benzoxy-bromo-benzene (18.4 g, 70.0 mmol) in THF (450 mL) at −78° C. was added BuLi (1.6M in hexane, 50.0 mL, 80.0 mmol). The mixture was stirred for 30 min at −78° C., and ZnCl2 (1M in THF, 86 mL, 86 mmol) was added. The mixture was allowed to warm up to rt. A sol. of 4-trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (WO 2004/002957; 19.5 g, 50.0 mmol) in THF (20 mL) and Pd(PPh3)4 (1.43 g, 1.23 mmol) were added. The mixture was quickly heated to 50° C., and stirred at this temperature for 40 min. Aq. sat. NH4Cl was added, and the mixture was extracted with EtOAc (3×). The combined org. extracts were washed with brine, dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:9→2:8) yielded the title compound (20.8 g, 98%). LC-MS: tR=1.12 min; ES+: 424.25.

Provenance & Evidence