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Water → 1-(2,3-Dimethylindazol-5-yl)-4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methoxy]pyridin-2-one

HRID 1497401
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1497401
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1.[F:20][C:21]([F:30])([F:29])[C:22]1[N:23]=[C:24]([CH2:27]O)[S:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:27][C:24]4[S:25][CH:26]=[C:22]([C:21]([F:30])([F:29])[F:20])[N:23]=4)=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 23560688(4-(Trifluoromethyl)-1,3-thiazol-2-yl)methanolHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Produkt 1

HCID 1177987801-(2,3-Dimethylindazol-5-yl)-4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methoxy]pyridin-2-oneAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (65 mg), [4-(trifluoromethyl)-1,3-thiazol-2-yl]methanol (73 mg) and triphenylphosphine (156 mg) in tetrahydrofuran (6 ml) was added bis(2-methoxyethyl)azodicarboxylate (140 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) and recrystallized from 2-propanol-diisopropyl ether to give the title compound (42 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)
  6. customrecrystallized from 2-propanol-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0d05120517f04f95802fd6749890c3d2
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09199963B2

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