1-(diphenylmethyl)-1H-indole-2,3-dione → HCID 67357402, Verbindung

HRID 1407476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1407476
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([Mg]Cl)(C)C.[C:16]1([CH:22]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[C:24]2=[O:33])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.ClCCl>[C:34]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([F:1])=[CH:3][C:4]=3[OH:10])([OH:32])[C:24]2=[O:33])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

6

Edukt 3

HCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 146616133-Fluoro-4-methoxyphenolHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 67357402HCID 67357402, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-fluoro-4-methoxyphenol (Niemann, M. B. J. Am. Chem. Soc. (1941), 63:609) (4.60 g, 32.4 mmol) in tetrahydrofuran (60 mL) at 5° C. was added a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (18.0 mL, 36.0 mmol). Tetrahydrofuran was removed under reduced pressure and dichloromethane (60 mL) was added. To the solution was added a solution of 1-(diphenylmethyl)-1H-indole-2,3-dione (8.00 g, 25.5 mmol) in dichloromethane (60 mL) at 5° C. and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with saturated ammonium chloride solution (5 mL). The reaction mixture was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was subjected to column chromatography with 40% to 90% gradient of ethyl acetate in hexanes to afford 1-(diphenylmethyl)-3-(4-fluoro-2-hydroxy-5-methoxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (6.60 g, 57%) as a pink solid: MS (ES+) m/z 438.3 (M−17).

Aufarbeitung

  1. customTetrahydrofuran was removed under reduced pressure and dichloromethane (60 mL)
  2. additionwas added
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution (5 mL)
  4. dry with materialThe reaction mixture was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-698bda693bd949f2a4b471b097c3c920
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916580B2

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