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Cesium carbonate → ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

HRID 1506400
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Reaktionsgleichung

Reaktionsgleichung von HRID 1506400
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]1([N:33]2[C:37]([C:38]([F:41])([F:40])[F:39])=[C:36]([C:42]3[O:46][N:45]=[C:44]4[C:47]5[C:52]([CH2:53][CH2:54][C:43]=34)=[CH:51][C:50]([CH:55]=[CH2:56])=[CH:49][CH:48]=5)[CH:35]=[N:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O>[C:1]1([C:7](=[N:14][CH:15]([CH2:56][CH2:55][C:50]2[CH:51]=[C:52]3[C:47](=[CH:48][CH:49]=2)[C:44]2=[N:45][O:46][C:42]([C:36]4[CH:35]=[N:34][N:33]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:37]=4[C:38]([F:40])([F:41])[F:39])=[C:43]2[CH2:54][CH2:53]3)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 671704203-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Produkt 1

HCID 86669896ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(diphenylmethyleneamino)acetate (315 mg, 1.178 mmol) in anhydrous dimethylsulfoxide (1 mL) was purged with nitrogen for 10 min before cesium carbonate (192 mg, 0.589 mmol) was added. The mixture was purged with nitrogen for 5 min. and stirred at room temperature for 30 min. Next, 3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 50A, 100 mg, 0.245 mmol) was added, the mixture was purged with nitrogen for 5 min and then stirred at 40° C. for 5 hr. The reaction mixture was cooled, diluted with water (10 mL), and extracted with ethyl acetate (3×5 mL). The ethyl acetate extracts were dried over sodium sulfate and concentrated under reduced pressure. Flash chromatography purification using an ISCO setup (4 g silica gel column, 10→100% ethyl acetate in hexanes) afforded ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (160 mg, 0.237 mmol, 97% yield) as a glassy solid. LC/MS M+1=675.4.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was purged with nitrogen for 5 min.
  3. customthe mixture was purged with nitrogen for 5 min
  4. stirringstirred at 40° C. for 5 hr
  5. temperatureThe reaction mixture was cooled
  6. additiondiluted with water (10 mL)
  7. extractionextracted with ethyl acetate (3×5 mL)
  8. dry with materialThe ethyl acetate extracts were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customFlash chromatography purification

Quellen und Nachweise

ORD-Eintrag
ord-001b29163840478499f508e0c39035b6
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216972B2

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