Boron tribromide → HCID 67777850, compound

HRID 1026230Notes

Reaction equation

HRID 1026230 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:9]2[C:5](=[CH:6][N:7]([C:12]3[CH:25]=[CH:24][C:15]([O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:14][CH:13]=3)[N:8]=2)[CH:4]=1.BrB(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[CH:11]=[CH:10][C:9]2[C:5](=[CH:6][N:7]([C:12]3[CH:13]=[CH:14][C:15]([O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:24][CH:25]=3)[N:8]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67777234HCID 67777234, compound

Product 1

HCID 67777850HCID 67777850, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-{(1S)-2-[4-(5-methoxy-2H-indazol-2-yl)phenoxy]-1-methylethyl}acetamide (70 mg) in dichloromethane (3 mL) was added dropwise a dichloromethane solution (1.0 M, 0.83 mL) of tribromoborane under ice-cooling, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (48 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe separated organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3d670d730833414da4791cc2b319ccfc
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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