Phosphorus oxychloride → 2-Chloro-6-(trifluoromethyl)-3H-imidazo[4,5-B]pyridine

HRID 730824Notes

Reaction equation

HRID 730824 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.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:10]1[NH:11][C:5]2[C:6]([N:9]=1)=[N:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2

Participants

3

Reactant 2

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

Product 1

HCID 116801682-Chloro-6-(trifluoromethyl)-3H-imidazo[4,5-B]pyridine

Procedure

A solution of 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one from step (c) above (161 mg, 0.789 mmol) in POCl3 (5 mL) was heated at 95° C. for 16 h. The reaction mixture was cooled to room temperature, the solvent was removed in vacuo and the resulting oily residue was purified by silica gel column chromatography, eluting with EtOAc/hexane (1:3) to give the title compound as a light-yellow solid. MS (ESI positive ion) m/z: 222 (M+1).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe resulting oily residue was purified by silica gel column chromatography
  3. washeluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-85827168ede349e38f1315c2197ad4c4
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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