Dimethylformamide → Methyl [(2-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-yl)oxy]acetate

HRID 534895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534895
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH3:29])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([OH:28])=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[N:20]([CH3:29])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:23][CH:22]=3)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 667511892-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-ol

Produkt 1

HCID 66751007Methyl [(2-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-yl)oxy]acetateAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-ol obtained in Example 28 (510 mg), methyl bromoacetate (239 mg), potassium carbonate (276 mg), and N,N-dimethylformamide (5 mL) was stirred at 60° C. for 3 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford crystals. Crystals were washed with diethyl ether and dried under reduced pressure to provide the title compound (509 mg, 84%) as crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto afford crystals
  6. washCrystals were washed with diethyl ether
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-084862cb41f6430fa2eefbd4e2439989
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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