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Cesium fluoride → 3-cyano-N-(2,4-dimethoxybenzyl)-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46361
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 46361
[C:1]([C:3]1[CH:4]=[C:5]([S:21]([N:24]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[O:39][CH3:40])[C:25]2[S:29][N:28]=[CH:27][N:26]=2)(=[O:23])=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1I)#[N:2].[F-].[Cs+].C([Sn](CCCC)(CCCC)[C:48]1[CH:53]=[CH:52][N:51]=[N:50][CH:49]=1)CCC>CN(C)C=O.[Cu]I>[C:1]([C:3]1[CH:4]=[C:5]([S:21]([N:24]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[O:39][CH3:40])[C:25]2[S:29][N:28]=[CH:27][N:26]=2)(=[O:23])=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[C:48]1[CH:53]=[CH:52][N:51]=[N:50][CH:49]=1)#[N:2]
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Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 594364853-cyano-N-(2,4-dimethoxybenzyl)-4-[2-iodo-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Produkt 1

HCID 594366013-cyano-N-(2,4-dimethoxybenzyl)-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A mixture of 3-Cyano-N-(2,4-dimethoxybenzyl)-4-[2-iodo-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 429, 33.07 g, 47.08 mmol) in dimethylformamide (140 mL) was treated with copper (I) iodide (1830 mg, 9.60 mmol) and cesium fluoride (14.4 g, 94.2 mmol). The mixture was sparged with nitrogen for 15 minutes. Then 4-(tributylstannyl)pyridazine (19.1 g, 51.8 mmol) dissolved in dimethylformamide (10 mL) was added and the reaction heated to 30° C. The reaction was cooled, poured onto water (1 L) and extracted with diethylether (4×450 mL). The combined extracts were washed with water (6×500 mL), dried over magnesium sulfate and evaporated to furnish an orange foam. This residue was purified using column chromatography (using a gradient of 100% heptane with 2% triethylamine to 40:60 ethylacetate:heptane with 2% triethylamine) to furnish the title compound as an off-white solid.

Aufarbeitung

  1. customThe mixture was sparged with nitrogen for 15 minutes
  2. additionwas added
  3. temperatureThe reaction was cooled
  4. additionpoured onto water (1 L)
  5. extractionextracted with diethylether (4×450 mL)
  6. washThe combined extracts were washed with water (6×500 mL)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto furnish an orange foam
  10. customThis residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-4cc6b565b70a4332b1b9cae758b25438
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541588B2

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