Dimethylformamide → (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate

HRID 563402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563402
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])C.[Na].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=O)=[CH:26][CH:27]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1.[CH3:37]N(C=O)C>C1COCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][C:25](/[C:29](/[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:2]/[C:4]([O:6][CH3:37])=[O:5])=[CH:26][CH:27]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 5360545SodiumHCID 53413272TrimethylphosphonoacetateHCID 67005723(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone

Produkt 1

HCID 59252822(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Trimethylphosphonoacetate (2.4 g, 13.4 mmol) was dissolved in 15 mL anhydrous DMF and treated with sodium hexadimethylsilazane (13.4 mmol, 1 M in THF). (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone (1.63 g, 5.16 mmol) was added and the reaction was heated to 85° C. for 16 hours. The following day, the cooled reaction was extracted from brine using ether×3 and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using 25% EtOAc in hexanes to give 1.74 g (91%) of (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate as a clear oil. MS found: (M+H)+=373.

Aufarbeitung

  1. customThe following day, the cooled reaction
  2. extractionwas extracted from brine
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel using 25% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7239e854cb5047679ec6649465c94480
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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