Triphenylphosphine → 1-(2,3-dimethyl-2H-indazol-5-yl)-4-{[5-(trifluoromethyl)thiophen-2-yl]methoxy}pyridin-2(1H)-one

HRID 1497372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497372
[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[S:26][C:25]([CH2:27]O)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[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:25]4[S:26][C:22]([C:21]([F:30])([F:29])[F:20])=[CH:23][CH:24]=4)=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 539255405-(Trifluoromethyl)-2-thiophenemethanolHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Produkt 1

HCID 1177986921-(2,3-dimethyl-2H-indazol-5-yl)-4-{[5-(trifluoromethyl)thiophen-2-yl]methoxy}pyridin-2(1H)-oneAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (100 mg), [5-(trifluoromethyl)thiophen-2-yl]methanol (143 mg) and triphenylphosphine (308 mg) in tetrahydrofuran (5 ml) was added bis(2-methoxyethyl)azodicarboxylate (275 mg) at 60° C., and the mixture was stirred at the same temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (71 mg).

Aufarbeitung

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-884b537e0dd74d17825e5129a71b29f8
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199963B2

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