4-Bromophenol → HCID 66727730, compound

HRID 573286Notes

Reaction equation

HRID 573286 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:3]2[N:2]([CH3:1])[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 66727730HCID 66727730, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (2.0 g), 4-bromophenol (4.9 g) and TEA (4.0 ml) was stirred at 120° C. for 3 h. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with 1 M NaOH aqueous solution, dried over Na2SO4, filtered and concentrated under reduced pressure. The residual crystals were recrystallized from AcOEt to give the title compound (1.7 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with 1 M NaOH aqueous solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residual crystals were recrystallized from AcOEt

Sources & evidence

ORD record
ord-2c83736a11944afcaef65995ddd8576f
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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