反应详情

To a solution of {3-[6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5-yl}methanol (Example 437, 49 mg, 0.0877 mmol) (1.5 mL) and N-iodosuccinimide (21 mg) in DCM at 0° C. was added trifluoroacetic acid (30 mg, 0.263 mmol). After stirring for 2 h, the reaction was quenched with 10% aqueous Na2S2O3 and the product was extracted with EtOAc. The combined extracts were washed with water, brine, dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography, eluting with 50% EtOAc in hexanes, to provide the title compound. LC/MS: m/e 586.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.55 (1H, d, J=1.8 Hz), 8.32 (1H, d, J=1.8 Hz), 7.64 (1H, d, J=7.6 Hz), 7.28 (1H, s), 7.20 (1H, J=7.5 Hz), 7.13 (2H, J=8.4 Hz), 6.86 (2H, J=8.5 Hz), 5.02 (2H, s), 4.30-5.0 (2H, br), 2.75 (1H, s br), 1.30 (9H, s).

1. customthe reaction was quenched with 10% aqueous Na2S2O3
2. extractionthe product was extracted with EtOAc
3. washThe combined extracts were washed with water, brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was purified by SiO2 column chromatography
7. washeluting with 50% EtOAc in hexanes