Water → HCID 17980396, compound
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][C:21]2[N:25]([CH3:26])[N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[N:14]=1.O>CC(N(C)C)=O>[CH3:19][C:17]1[CH:18]=[C:13]([N:5]2[CH:4]=[C:3]([C:2]([F:9])([F:8])[F:1])[CH:7]=[N:6]2)[N:14]=[C:15]([O:20][C:21]2[N:25]([CH3:26])[N:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=2)[CH:16]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
0.385 g of 4-trifluoromethylpyrazole is introduced under nitrogen in 10 ml of dimethylacetamide and at 0° C. 0.096 g of NaH is added. The mixture is allowed to come to RT over 30 min and then 0.757 g of 2-chloro-4-methyl-6-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine is added and the mixture is heated at 140° C. for 7 h, cooled to RT and poured into water. The product is extracted twice with ethyl acetate/heptane (1:1) and twice with ethyl acetate and then washed with water and saturated sodium chloride solution, dried over MgSO4 and concentrated. Chromatographic purification on silica gel gives 0.332 g of 4-methyl-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-6-(4-trifluoromethylpyrazol-1-yl)pyridine as white crystals.
Workup
- temperaturecooled to RT
- extractionThe product is extracted twice with ethyl acetate/heptane (1:1) and twice with ethyl acetate
- washwashed with water and saturated sodium chloride solution
- dry with materialdried over MgSO4
- concentrationconcentrated
- customChromatographic purification on silica gel
Sources & evidence
- ORD record
- ord-c358e12b55b34dc0ba1eb4cef4435b9a
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282469B2
Reaction notes
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