Boron tribromide → HCID 11705499, compound

HRID 1786019Notes

Reaction equation

HRID 1786019 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:33])[C:23]3[CH:28]=[C:27]([F:29])[C:26]([O:30]C)=[C:25]([F:32])[CH:24]=3)[C@@H:14]([CH3:34])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:33])[C:23]3[CH:28]=[C:27]([F:29])[C:26]([OH:30])=[C:25]([F:32])[CH:24]=3)[C@@H:14]([CH3:34])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57595496HCID 57595496, compound

Product 1

HCID 11705499HCID 11705499, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (200 mg, 0.41 mmol) was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 3.0 mL) was added; the reaction mixture was stirred at room temperature for until no starting material remained. The reaction mixture was washed with sat. NaHCO3 and brine carefully. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography using Hexanes-EtOAc system to give N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (152 mg, 78%).

Workup

  1. washThe reaction mixture was washed with sat. NaHCO3 and brine carefully
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b2b9ea51be7b485ea06c0c3cbdacbeab
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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