Phosphorus oxychloride → HCID 178478308, compound

HRID 496273Notes

Reaction equation

HRID 496273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)[NH:8][C:5]2=[N:6][CH:7]=1.O=P(Cl)(Cl)[Cl:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([Cl:14])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19244136-bromo-3H-imidazo[4,5-b]pyridin-2-ol

Product 1

HCID 178478308HCID 178478308, compound

Procedure

Reflux 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (5 g) for 14 h in POCl3 (50 mL). Evaporate the solvent in vacuo, then carefully neutralize with saturated NaHCO3, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, and purify by flash chromatography (1:1 hexanes/EtOAc) to obtain 6-bromo-2-chloro-3H-imidazo[4,5-b]pyridine. B. 6-Bromo-2-(spiro[isobenzofuran-1,4′piperidin]-3-one-3H-imidazo[4,5-b]pridine

Workup

  1. customEvaporate the solvent in vacuo
  2. extractionextract with EtOAc
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate under vacuum
  5. custompurify by flash chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-72021817a16b4515a5d119d6ef01e77b
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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