Boron tribromide → HCID 11705499, compound

HRID 1785993Notes

Reaction equation

HRID 1785993 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, 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-(3,5-difluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (152 mg, 78%).

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-3061ed6efacc4b96a7b16685ded4c08a
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…