Boron tribromide → HCID 178516338, compound

HRID 1360674Notes

Reaction equation

HRID 1360674 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]2[C:14]([CH:15]=[C:16]([O:18]C)[CH:17]=1)=[C:13]([C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27])[C:12](=[O:28])[CH:11]=[CH:10]2.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]2[C:14]([CH:15]=[C:16]([OH:18])[CH:17]=1)=[C:13]([C:20]1[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=1[Cl:26])[C:12](=[O:28])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 16064459HCID 16064459, compound

Product 1

HCID 178516338HCID 178516338, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-8-methoxy-2H-quinolizin-2-one (Example 14, 40 mg) in methylene chloride was added boron tribromide (0.06 mL) at −78° C. The mixture was warmed to room temperature and stirred for 12 h. After quenching with 2N HCl, the mixture was extracted with methylene chloride, washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel (methylene chloride/methano-=7/1) to give title compound (25 mg).

Workup

  1. customAfter quenching with 2N HCl
  2. extractionthe mixture was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel (methylene chloride/methano-=7/1)

Sources & evidence

ORD record
ord-cbdd8768dc864f358df891681d38d88c
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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