Phthalimide → 2-[(3-Chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-isoindole-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methanol (12.0 g, 38.4 mmol), phthalimide (11.30 g, 76.8 mmol) and triphenylphosphine (20.10 g, 76.8 mmol) in THF (150 mL) in a flame-dried flask was added diisopropylazodicarboxylate (15.2 mL, 76.8 mmol) drop wise under nitrogen atmosphere. The reaction mixture was stirred at 60° C. for 16 h. TLC (EtOAc/Hexanes, 1:1) showed no starting material left. Solvent was then evaporated to give a crude residue which was purified through column on silica gel using EtOAc/Hexanes (1:1). Yield: 10.5 g (61%); 1H NMR (CDCl3, 300 MHz) δ 6.91 (s, 1H), 7.01-7.22 (m, 5H), 7.39-7.43 (m, 4H), 7.78-7.82 (m, 2H), 7.89-7.94 (m, 2H), 8.40 (d, J=2.4 Hz, 1H), 8.58 (d, J=2.4 Hz, 1H).

Provenance & Evidence