Boron tribromide → 2,4-Dichloro-6-hydroxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

HRID 1868426Notes

Reaction equation

HRID 1868426 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9]C)[C:3]=1[S:11]([NH:14][CH:15]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[C:16]([F:19])([F:18])[F:17])(=[O:13])=[O:12].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([OH:9])[C:3]=1[S:11]([NH:14][CH:15]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[C:16]([F:18])([F:19])[F:17])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 116984292,4-Dichloro-6-methoxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

Product 1

HCID 116838782,4-Dichloro-6-hydroxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamideYield 14.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 30 mg (0.06 mmol) of 2,4-dichloro-6-methoxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide in 2 mL of dichloromethane was added 1 mL (1 mmol) of 1 M boron tribromide in CH2Cl2. After 1 hour, the reaction was cooled in an ice-water bath and cautiously quenched with 5-10 mL of methanol with stirring. The mixture was warmed to room temperature and the residue was dissolved in ethyl acetate and washed with three 20 mL portions of 1 M aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine. The organic layers was dried over sodium sulfate, decanted, and concentrated in vacuo. The product crystallized upon concentration to afford 4 mg (13%) of the title compound.

Workup

  1. temperaturethe reaction was cooled in an ice-water bath
  2. customcautiously quenched with 5-10 mL of methanol
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with three 20 mL portions of 1 M aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine
  5. dry with materialThe organic layers was dried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated in vacuo
  8. customThe product crystallized upon concentration

Sources & evidence

ORD record
ord-e8979d9d21c944d48669c2b83a3cbb5c
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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