Boron tribromide → HCID 22339409, compound

HRID 585134Notes

Reaction equation

HRID 585134 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([N:28]2[C:33](=[O:34])[NH:32][C:31](=[O:35])[CH:30]=[N:29]2)[CH:25]=[C:24]([Cl:36])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:22]C)=[C:9]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:10]=1.B(Br)(Br)Br>ClCCl>[Cl:36][C:24]1[CH:25]=[C:26]([N:28]2[C:33](=[O:34])[NH:32][C:31](=[O:35])[CH:30]=[N:29]2)[CH:27]=[C:2]([Cl:1])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:22])=[C:9]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22339517HCID 22339517, compound

Product 1

HCID 22339409HCID 22339409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of N-{5-[2,6-dichloro-4-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-phenoxy]-2-methoxy-phenyl}-4-fluoro-benzenesulfonamide (96 mg) in dichloromethane (5 mL) was added boron tribromide (64 μL) and the resulting solution was allowed to stir at ambient temperature for 4 h. The reaction mixture was poured over ice, stirred for 0.5 h and extracted with ethyl acetate. The organic phase was dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (40% acetone/hexanes) to afford the title compound of this EXAMPLE as a colorless foam, 68 mg. m.p. 222-225° C. (dec), MS Calc.:539.2 Found:536.8.

Workup

  1. additionThe reaction mixture was poured over ice
  2. stirringstirred for 0.5 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo and flash
  6. customchromatographed on silica gel (40% acetone/hexanes)

Sources & evidence

ORD record
ord-49f421754d9f4c27893a2300b0cf051f
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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