Boron tribromide → HCID 86599917, compound

HRID 1443157Notes

Reaction equation

HRID 1443157 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH:11]=[N:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16](=[O:22])[NH:17]3)=[C:4]([O:30]C)[CH:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:25])([F:24])[F:26])[CH:11]2[NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16](=[O:22])[NH:17]3)=[C:4]([OH:30])[CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 17989256HCID 17989256, compound

Product 1

HCID 86599917HCID 86599917, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

235.9 mg of 4-{[4-(4bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidene]amino}-1,3-dihydroindol-2-one is mixed at 0° C. with 6.42 ml of a 1 M solution of BBr3 in dichloromethane and stirred for four hours at room temperature. At 0° C., saturated sodium bicarbonate solution is carefully added in drops. After being extracted three times with ethyl acetate, the organic phases are dried on sodium sulfate. The desiccant is suctioned off, and the solvent is spun off. The residue is chromatographed on a Flashmaster. 125.4 mg (54%) of the desired compound is isolated.

Workup

  1. extractionAfter being extracted three times with ethyl acetate
  2. customthe organic phases are dried on sodium sulfate
  3. customThe residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-79050c713344414abce99a7f46d210c8
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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