Water → 2-(4-Trifluoromethylpyrazol-1-yl)-6-(2-trifluoromethyl-4-thienyloxy)pyridine

HRID 1793772Notes

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[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[S:23][CH:24]=2)[N:14]=1.O>CC(N(C)C)=O>[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[S:23][CH:24]=3)[N:14]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.114 g of 4-trifluoromethylpyrazole is introduced in 5 ml of dimethylacetamide under nitrogen and at 0° C. 0.028 g of NaH is added. The mixture is allowed to come to RT over 30 min and then 0.2 g of 2-fluoro-6-(2-trifluormethyl-4-thienyloxy)pyridine is added and the mixture is heated at 80° C. for 9 h, cooled to RT and poured into water. After threefold extraction with ethyl acetate the product is washed with water and saturated sodium chloride solution, dried over MgSO4 and concentrated. Chromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent gives 0.043 g of 2-(4-trifluoromethylpyrazol-1-yl)-6-(2-trifluoromethyl-4-thienyloxy)pyridine as colorless crystals.

Workup

temperaturecooled to RT
extractionAfter threefold extraction with ethyl acetate the product
washis washed with water and saturated sodium chloride solution
dry with materialdried over MgSO4
concentrationconcentrated
customChromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent

Sources & evidence

ORD record: ord-d329a900d7cb40b4b85079a41e5dd220
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022650B2

Reaction notes

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