Methanol → HCID 90103359, compound

HRID 1052644Notes

Reaction equation

HRID 1052644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][C:13]=2[F:20])(=[O:11])=[O:10])[CH:5]=[N:6][CH:7]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[F:20])(=[O:10])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 90102463HCID 90102463, compound

Product 1

HCID 90103359HCID 90103359, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(5-Bromopyridin-3-yl)-2-fluoro-4-methoxybenzenesulfonamide (692 mg, 1.92 mmol) was dissolved in DCM (10 ml), the reaction flask was sealed and boron tribromide (5 ml, 1M solution in DCM) was added dropwise under an argon atmosphere. After stirring overnight at reflux, more boron tribromide was added (5 ml) and the mixture was refluxed for 18 h. After cooling in an ice bath, methanol was added dropwise and evaporated under reduced pressure. The mixture was poured into ice and extracted with ethyl acetate. The resulting organic solution was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The product was purified by flash chromatography (0% to 5% DCM/MeOH) to give 414 mg (62% yield) of the title compound as a white solid.

Workup

  1. customthe reaction flask was sealed
  2. temperatureat reflux
  3. temperaturethe mixture was refluxed for 18 h
  4. temperatureAfter cooling in an ice bath
  5. customevaporated under reduced pressure
  6. additionThe mixture was poured into ice
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic solution was washed with water and brine
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customthe solvents were removed under reduced pressure
  12. customThe product was purified by flash chromatography (0% to 5% DCM/MeOH)

Sources & evidence

ORD record
ord-32834153e88a494b86ee6cb4decc0d62
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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