Phosphorus oxychloride → HCID 178432416, compound

HRID 2102393Notes

Reaction equation

HRID 2102393 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:12]=[CH:11][NH:10][C:5]2=[N+:6]([O-])[C:7]=1[CH3:8].C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:20]>>[Br:1][C:2]1[C:3]([Cl:20])=[C:4]2[N:12]=[CH:11][NH:10][C:5]2=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178421691HCID 178421691, compound

Product 1

HCID 178432416HCID 178432416, compound

Procedure

A solution of 6-bromo-5-methyl-3H-imidazo[4,5-b]pyridine 4-oxide (1.00 equivalent) in POCl3 (excess) is stirred at 80° C. for 16 hours. The reaction mixture is concentrated in vacuo to give the crude material that is poured into ice-water. The resulting aqueous solution is neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product. The product is purified by trituration or flash column chromatography if further purification is necessary.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customto give the crude material that
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a055926522044f018aa8f47cee99f41f
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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