Boron tribromide → HCID 68920573, compound

HRID 1785999Notes

Reaction equation

HRID 1785999 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:32])[C:23]3[CH:28]=[CH:27][C:26]([O:29]C)=[C:25]([F:31])[CH:24]=3)[C@@H:14]([CH3:33])[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:3]=[CH:4][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:32])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:31])[CH:24]=3)[C@@H:14]([CH3:33])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68924381HCID 68924381, compound

Product 1

HCID 68920573HCID 68920573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-chlorophenyl)-N-[(2S,4R)-1-(3-fluoro-4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 10 mL) was added; the reaction was allowed to stir at room temperature for until no starting material remained. The reaction was washed with sat. NaHCO3 and brine. The organic layer were dried over MgSO4, filtered and concentrated down. The residue was purified by flash chromatography using hexanes-ethyl acetate system to give N-(4-chlorophenyl)-N-[(2S,4R)-1-(3-fluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide in decent yield.

Workup

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

Sources & evidence

ORD record
ord-b720726e9c70432e8a451e15e34acb90
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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