Boron tribromide → HCID 22339645, compound

HRID 585143Notes

Reaction equation

HRID 585143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([Cl:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([S:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])[CH:10]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([Cl:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([S:17]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)(=[O:18])=[O:19])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22339615HCID 22339615, compound

Product 1

HCID 22339645HCID 22339645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-{3,5-dichloro-4-[4-methoxy-3-(piperidine-1-sulfonyl)-phenoxy]-phenyl}-2H-[1,2,4]triazine-3,5-dione (0.5 g) in dichloromethane (30 mL) was added boron tribromide (0.3 mL) and the resulting heterogeneous mixture was allowed to stir at room temperature for 6 h. Ice was added to the mixture and the resulting two-phase solution stirred for 1 h. Layers were separated and the organic phase was washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford an oil. Flash chromatography on silica gel (35% acetone/hexanes) afforded the title compound of this EXAMPLE as a colorless solid, 0.4 g. MS Calc.:513.4 Found:512.9.

Workup

  1. additionIce was added to the mixture
  2. stirringthe resulting two-phase solution stirred for 1 h
  3. customLayers were separated
  4. washthe organic phase was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto afford an oil

Sources & evidence

ORD record
ord-255d65ed3e83401e952ffc1d7a0aa3d3
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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