Boron tribromide → HCID 86708219, compound

HRID 923777Notes

Reaction equation

HRID 923777 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24][CH2:25][CH3:26])[N:15]([CH3:27])[C:12]2=[N:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:25]([S:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[N:15]([CH3:27])[C:12]2=[N:13][CH:14]=[C:9]([OH:8])[CH:10]=[C:11]2[N:17]=1)[CH3:26]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68091237HCID 68091237, compound

Product 1

HCID 86708219HCID 86708219, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 6-benzyloxy-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine 262 mg, and chloroform (3 mL), boron tribromide (1M in dichloromethane) (698 μL) was added under ice-cooling, and stirred for 3 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with chloroform then ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 168 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-ol (hereinafter, Present Compound 268).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f8f8f49772049638e669737180ceec1
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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