Boron tribromide → HCID 57800484, compound

Temperature

-78 °C

To a solution of 4-chloro-2-(difluoromethyl)-5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indole (2.6 g, 5.82 mmol) in anhydrous CH2Cl2 (80 mL), under N2, at −78° C., was slowly added a solution of BBr3 in CH2Cl2 (1M, 6.1 mL). After stirring at −78° C. for 30 min, additional BBr3 solution (1M, 0.3 mL) was added and stirring was continued at −78° C. for 30 min. While at −78° C., sat'd aqueous NaHCO3 solution (˜10 mL) was added slowly, the cold bath was then removed and the reaction mixture brought to rt. The mixture was partitioned between CH2Cl2 and sat'd NaHCO3 solution. The aqueous phase was washed with CH2Cl2. The combined organic phases were washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-40% EtOAc-hexanes gradient) to afford the title compound (1.87 g, 89% yield): 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J=9.0 Hz, 1H), 7.89 (d, J=7.6 Hz, 2H), 7.58 (t, J=7.6 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 7.32 (t, J=54.2 Hz, 1H), 7.12-7.08 (m, 2H), 5.42 (bs, 1H); MS (ES) m/z 356 (M−1).

1. stirringstirring
2. waitwas continued at −78° C. for 30 min
3. customWhile at −78° C.
4. additionwas added slowly
5. customthe cold bath was then removed
6. custombrought to rt
7. customThe mixture was partitioned between CH2Cl2
8. washThe aqueous phase was washed with CH2Cl2
9. washThe combined organic phases were washed with sat'd brine
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated in vacuo
12. customThe residue was purified by flash chromatography (0-40% EtOAc-hexanes gradient)

ORD record

ord-f74e68dd2bd449fe9af8d278be987dc9

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572820B2