Benzene → HCID 15463646, compound

To a stirred solution of (2-hydroxybenzoyl)-2-bromopyrrole (0.26 g, 1.0 mmol, from Example C) in 5 mL of dry benzene at room temperature in an atmosphere of nitrogen, was added sodium methoxide (60 mg, 1.1 mmol). After 5 min, CuBr (22 mg, 0.15 mmol) and DMF (5 mL) were added. The reaction mixture was stirred at room temperature for 1 hr, and then stirred at 100° C. overnight. The solvent was removed in vacuo, and 30 mL of CH2Cl2 was added. The solution was washed with sat. aq. NaHCO3, water, and brine. The organic layer was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by chromatography, using EtOAc-Hex (5:95) as the eluent, to give 51.8 mg of the title compound: mp 129-130° C. 1H NMR (CDCl3) δ 8.28 (1 H, dd, J=6.8, 1.8), 7.76-7.67 (1 H, m), 7.40-7.25 (3 H, m), 6.49 (1 H, t, J=3.5), 5.88 (1 H, dd, J=3.5, 1.8).

1. stirringstirred at 100° C. overnight
2. customThe solvent was removed in vacuo, and 30 mL of CH2Cl2
3. additionwas added
4. washThe solution was washed with sat. aq. NaHCO3, water, and brine
5. dry with materialThe organic layer was dried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by chromatography

ORD record

ord-e5914987007d4c74be7b1d56d10a181e

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057315