Phosphorus oxychloride → 2-Chloro-3-cyclohexyl-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate

HRID 1890358Notes

Reaction equation

HRID 1890358 reaction equation
[CH3:1][S:2]([O:5][C:6]1[N:11]=[C:10]2[N:12]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:13](O)=[N:14][C:9]2=[CH:8][CH:7]=1)(=[O:4])=[O:3].O=P(Cl)(Cl)[Cl:24]>>[CH3:1][S:2]([O:5][C:6]1[N:11]=[C:10]2[N:12]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:13]([Cl:24])=[N:14][C:9]2=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178505196HCID 178505196, compound

Product 1

HCID 866552622-Chloro-3-cyclohexyl-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate

Conditions

Temperature
80 °C

Procedure

3-Cyclohexyl-2-hydroxy-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate (0.4 g, 1.285 mmol) and POCl3 (2.395 ml, 25.7 mmol) were placed in a sealed tube and heated to 80° C. for 48 h. The volatiles were removed under reduced pressure. The residue was dissolved in aqueous NaHCO3 giving a basic solution. The solution was further diluted with water and extracted with EtOAc. The combined organics was dried over MgSO4 and concentrated to give the title compound without further purification. LCMS m/z=330.30 [M+H]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in aqueous NaHCO3 giving a basic solution
  3. additionThe solution was further diluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fad94973a17643529353dace7a9a58b8
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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