Phosphorus tribromide → 2-((4-Bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole

HRID 1778284Notes

Reaction equation

HRID 1778284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:26]>CN(C=O)C>[Br:26][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:20]3[S:21][CH:22]=[CH:23][N:24]=3)[CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1785163976-((4-Chlorophenyl)(thiazol-2-yl)methyl)quinolin-4-ol

Product 1

HCID 1183239902-((4-Bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-4-ol (500 mg, 1.417 mmol, 1 equip) was dissolved in DMF (4 mL) and phosphorus tribromide (766 mg, 2.834 mmol, 2 equip) was added dropwise. A red-brown precipitate formed immediately and was collected to yield 2-((4-bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole which was used in the next step without purification.

Workup

  1. customA red-brown precipitate formed immediately
  2. customwas collected

Sources & evidence

ORD record
ord-f5aa49c64cec47c8aadbd708d097d186
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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