Boron tribromide → HCID 53245809, compound

HRID 1915520Notes

Reaction equation

HRID 1915520 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([NH:13][C:14]([C:16]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([NH:13][C:14]([C:16]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59410053HCID 59410053, compound

Product 1

HCID 53245809HCID 53245809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-methoxy-2-naphthyl)-4-oxo-1H-quinoline-3-carboxamide (73 mg, 0.21 mmol) in DCM (4 mL) was added BBr3 (1.1 mL, 11.64 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 then was heated to 50° C. for 2 h, cooled to −10° C. and quenched with saturated solution of NaHCO3. The aqueous layer was extracted with DCM and the combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via reverse phase HPLC to get N-(4-hydroxy-2-naphthyl)-4-oxo-1H-quinoline-3-carboxamide. LC/MS: m/z 331 (M+H)+ at 1.47 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customthe resulting reaction mixture
  4. temperaturewas heated to 50° C. for 2 h
  5. temperaturecooled to −10° C.
  6. customquenched with saturated solution of NaHCO3
  7. extractionThe aqueous layer was extracted with DCM
  8. dry with materialthe combined organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-7d1fc707a4c3413c984674fa5b6f7b45
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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