Water → 3-Benzyl-4-bromo-8-trifluoromethyl-cinnoline

HRID 643340Notes

Reaction equation

HRID 643340 reaction equation
[CH2:1]([C:8]1[N:9]=[N:10][C:11]2[C:16]([C:17]=1O)=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:25])=O.O>CN(C=O)C>[CH2:1]([C:8]1[N:9]=[N:10][C:11]2[C:16]([C:17]=1[Br:25])=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 178515565HCID 178515565, compound

Product 1

HCID 685814793-Benzyl-4-bromo-8-trifluoromethyl-cinnolineYield 105.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-benzyl-8-trifluoromethyl-cinnolin-4-ol (1.6 g, 4.4 mmol) and POBr3 (2.5 g, 8.7 mmol) in DMF (30 ml) was heated to 75° C. After 1 hr, the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc which was dried (MgSO4) and concentrated to give a solid. The solid was triturated with MeOH and filtered to give 3-benzyl-4-bromo-8-trifluoromethyl-cinnoline (1.7 g). MS (ES) m/z 366.7.

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc which
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was triturated with MeOH
  7. filtrationfiltered

Sources & evidence

ORD record
ord-33c630b8d2a04047b59cfe702246ab30
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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