Water → HCID 17980395, compound

HRID 1180475Notes

Reaction equation

HRID 1180475 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[N:24]([CH3:25])[N:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[N:14]=1.O>CC(N(C)C)=O>[CH3:25][N:24]1[C:20]([O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([N:5]3[CH:4]=[C:3]([C:2]([F:9])([F:8])[F:1])[CH:7]=[N:6]3)[N:14]=2)=[CH:21][C:22]([C:26]([F:29])([F:27])[F:28])=[N:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 127777954-(Trifluoromethyl)-1H-pyrazoleHCID 17980398HCID 17980398, compound

Product 1

HCID 17980395HCID 17980395, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

0.262 g of 4-trifluoromethylpyrazole is introduced under nitrogen in 7 ml of dimethylacetamide and at 0° C. 0.057 g of NaH is added. The mixture is allowed to come to RT over 30 min and then 0.5 g of 2-fluoro-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), washed with water and saturated sodium chloride solution, dried over MgSO4 and concentrated. Chromatographic purification on silica gel gives 0.349 g of 2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-6-(4-trifluoromethylpyrazol-1-yl)pyridine as white crystals.

Workup

  1. temperaturecooled to RT
  2. extractionThe product is extracted twice with ethyl acetate/heptane (1:1)
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-bb8d4d8810c94f2b8ffaade1106debe1
Source dataset
uspto-grants-2007_10
Patent number
US07282469B2

Reaction notes

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