Boron tribromide → HCID 57473932, compound

HRID 1868425Notes

Reaction equation

HRID 1868425 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([NH:13][CH:14]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:29]C)[CH:27]=2)[NH:22][CH:21]=1)[C:15]([F:18])([F:17])[F:16])(=[O:12])=[O:11].B(Br)(Br)Br>ClCCl>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[S:10]([NH:13][CH:14]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([OH:29])[CH:27]=2)[NH:22][CH:21]=1)[C:15]([F:18])([F:16])[F:17])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11655098HCID 11655098, compound

Product 1

HCID 57473932HCID 57473932, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 60 mg (0.14 mmol) of 2,4,6-trimethyl-N-[2,2,2-trifluoro-1-(5-methoxy-1H-indol-3-ylmethyl)ethyl]benzenesulfonamide in 1 mL of anhydrous dichloromethane was slowly added 0.34 mL (0.34 mmol) of a 1 M solution of boron tribromide in dichloromethane. After 3 hours at room temperature, the reaction was cooled in ice, quenched with 0.5 mL of cold water and stirred for 5 minutes. The reaction mixture was diluted with 50 mL of dichloromethane, filtered through CELITE® filter aid, and concentrated in vacuo. The crude mixture was purified by preparative TLC eluting with dichloromethane-ethyl acetate (85:15) to afford 35 mg (60%) of the title compound as an off-white solid.

Workup

  1. temperaturethe reaction was cooled in ice
  2. customquenched with 0.5 mL of cold water
  3. additionThe reaction mixture was diluted with 50 mL of dichloromethane
  4. filtrationfiltered through CELITE®
  5. filtrationfilter aid
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by preparative TLC
  8. washeluting with dichloromethane-ethyl acetate (85:15)

Sources & evidence

ORD record
ord-4db28e8cc76d4a76b0ce4357d0e5e29b
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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