Hydrochloric Acid → HCID 59309885, compound

HRID 1513000Notes

Reaction equation

HRID 1513000 reaction equation
[F:1][C:2]1[C:3]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])=[CH:4][C:5]([S:10]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[C:6]([O:8]C)[CH:7]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[F:1][C:2]1[C:3]([N:24]2[C:25](=[O:34])[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]2=[O:33])=[CH:4][C:5]([S:10]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:11])=[O:12])=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 685144615-fluoro-2-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)anisole

Product 1

HCID 59309885HCID 59309885, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-fluoro-2-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl-sulfonyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)anisole (0.57 g) in methylene chloride (12 mL) was added boron tribromide (1 mol/L methylene chloride solution, 3.53 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.46 g).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3a39546a4deb4d2b99fdfd16e6175a62
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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