Phosphorus tribromide → HCID 86683085, compound

HRID 1497270Notes

Reaction equation

HRID 1497270 reaction equation
[CH:1]1([C:6]2[C:15]([C:16]#[N:17])=[C:14](O)[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:12]=3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Br)(Br)[Br:24]>CN(C=O)C>[Br:24][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:12]=2)[N:7]=[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:15]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178509374HCID 178509374, compound

Product 1

HCID 86683085HCID 86683085, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyclopentyl-4-hydroxy-6-trifluoromethyl-quinoline-3-carbonitrile (200 mg, 490 μmol) in DMF (2.00 ml) was added phosphorus tribromide (1.47 ml, 1.47 mmol) dropwise at 0° C. The reaction mixture was allowed to reach room temperature and stirring was continued for 20 h. The mixture was concentrated in vacuo and the remaining residue was poured on water. The mixture was extracted with EtOAc and the combined extracts were dried with Na2SO4 and evaporated. The resulting yellow solid was purified by column chromatography (silica gel, dichloromethane) to afford the title compound (139 mg, 77%) as white solid. MS (ESI): 369.5 (M+H)+.

Workup

  1. customto reach room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe remaining residue was poured on water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe combined extracts were dried with Na2SO4
  6. customevaporated
  7. customThe resulting yellow solid was purified by column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-429ce4d6420d4a76a5579e9c96438cb4
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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