Phosphorus oxychloride → HCID 178506240, compound

HRID 496271Notes

Reaction equation

HRID 496271 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[NH:11][C:10](=O)[NH:9][C:6]2=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:17])=O>[Cl-].C[N+](C)(C)C>[Cl:17][C:10]1[NH:9][C:6]2=[N:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=[C:5]2[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 117153916-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 178506240HCID 178506240, compound

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

Heat a solution of 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one. (0.6 g, 2.95 mmol) and tetramethylammonium chloride (0.3 g) to 110° C. in phosphorus oxychloride (10 mL) for 10 hours. After cooling, remove the excess POCl3 in vacuo, and then neutralize with saturated NaHCO3, extract with EtOAc. Dry over Na2SO4, concentrate under vacuum to obtain 2-chloro-6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine. D. 1′-(6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine-2-yl)-spiro[isobenzofuran-1,4′-piperidin-3-one

Workup

  1. temperatureAfter cooling
  2. customremove the excess POCl3 in vacuo
  3. extractionextract with EtOAc
  4. dry with materialDry over Na2SO4
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-b0b013631d2449f9a889a3ddc64e7495
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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