Phosphorus oxychloride → 2-Chloro-6-(trifluoromethyl)-3H-imidazo[4,5-B]pyridine
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]=2Participants
3
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
- customthe solvent was removed in vacuo
- customthe resulting oily residue was purified by silica gel column chromatography
- 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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