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

HRID 912884Notes

Reaction equation

HRID 912884 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-22ddb6c502004759a57a6e62f6d76188
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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