Phosphorus oxychloride → 5-Chloro-3-(trifluoromethyl)-1,6-naphthyridine
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[CH:8][NH:9][C:10](=O)[C:11]=2[CH:12]=1.P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:18][C:10]1[N:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=[N:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Into a 50 mL round-bottom flask, was placed a solution of 3-(trifluoromethyl)-1,6-naphthyridin-5(6H)-one (as prepared in the previous step, 1 g, 4.67 mmol, 1.00 equiv) in acetonitrile (10 mL) and phosphoryl trichloride (10 mL). The reaction mixture was stirred for 2 h at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:20). The title compound was obtained as a yellow solid.
Workup
- customInto a 50 mL round-bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- customThe residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:20)
Sources & evidence
- ORD record
- ord-525b3c9d78b64361a2ffc11548e1df42
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518969B2
Reaction notes
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