Boron tribromide → HCID 59410100, compound

HRID 2404922Notes

Reaction equation

HRID 2404922 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[CH:7][C:6]=1[NH:16][C:17]([C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][C:24]([O:30]C)=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[CH:7][C:6]=1[NH:16][C:17]([C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][C:24]([OH:30])=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:18])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59410073HCID 59410073, compound

Product 1

HCID 59410100HCID 59410100, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-di-tert-butyl-5-hydroxy-phenyl)-7-methoxy-4-oxo-1H-quinoline-3-carboxamide (120 mg, 0.28 mmol) in DCM (1.5 mL) was added BBr3 (1.5 mL, 15.23 mmol) dropwise at −78° C. After the addition was complete the cooling bath was removed and the resulting reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with sat. solution of NaHCO3. The aqueous layer was extracted with DCM and the combined organic layer was dried over MgSO4, filtered and concentrated. The residue was purified via reverse phase HPLC to give N-(2,4-ditert-butyl-5-hydroxy-phenyl)-7-hydroxy-4-oxo-1H-quinoline-3-carboxamide. LC/MS: m/z 409.5 (M+H)+ at 1.83 min (10%-99% CH3 CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customthe resulting reaction mixture
  4. customThe reaction mixture was quenched with sat. solution of NaHCO3
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-7f69c388686043c38f4367dab87c00e5
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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