反应详情

A suspension of ethyl 5-bromo-2-(4-fluorophenyl)-1H-indole-3-carboxylate (90 mg, 0.25 mmol) in 1,2-dichloroethane (3 mL) was cooled in an ice bath under an atmosphere of N2. A solution of boron tribromide in CH2Cl2 (1M, 0.75 mL, 0.75 mmol) was added the reaction was allowed warm to r.t. under N2 over 4 h. Then the reaction was then quenched by the addition of a solution of methylamine in THF (2 M, 5 mL, 10 mmol). The reaction was partitioned between EtOAc and water, the organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated to give a colorless oil. Et2O/hexanes was added and a white precipitate formed. The powder was collected by filtration, washed with Et2O, and air dried to give the title compound (60 mg, 70% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.93 (s, 1H) 7.82 (d, J=1.83 Hz, 1H) 7.71-7.78 (m, 3H) 7.32-7.41 (m, 3H) 7.29 (dd, J=8.55, 1.83 Hz, 1H) 2.75 (d, J=4.58 Hz, 3H). LC/MS was performed on a Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. LC/MS method: solvent A=5% CH3CN/95% H2O/10 mM NH4OAc, solvent B=95% CH3CN/5% H2O/10 mM NH4OAc, start % B=0, final % B=100, gradient time=2 min, stop time=3 min, flow rate=5 ml/min, column: XBridge C18 5 μm 4.6×50 mm; HPLC Rt=1.26, (ES+) m/z (MH+)=347, 349 (1:1 ratio).

1. temperaturewas cooled in an ice bath under an atmosphere of N2
2. customThe reaction was partitioned between EtOAc and water
3. washthe organic phase was washed with water and brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a colorless oil
8. customa white precipitate formed
9. filtrationThe powder was collected by filtration
10. washwashed with Et2O, and air
11. customdried