Ammonium Chloride → 3-[6-[tert-butylsilyloxy(diphenyl)methyl]-2-methylimidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione

HRID 216675

Reaktionsgleichung

Reaktionsgleichung von HRID 216675
CC(C)([O-])C.[K+].CO[C:9](=[O:21])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=O.[C:22]([SiH2:26][O:27][C:28]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:29]1[CH:30]=[CH:31][C:32]2[N:33]([C:35]([CH2:39][C:40]([NH2:42])=[O:41])=[C:36]([CH3:38])[N:37]=2)[CH:34]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O>[C:22]([SiH2:26][O:27][C:28]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:29]1[CH:30]=[CH:31][C:32]2[N:33]([C:35]([C:39]3[C:40](=[O:41])[NH:42][C:9](=[O:21])[C:10]=3[C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)=[C:36]([CH3:38])[N:37]=2)[CH:34]=1)([CH3:25])([CH3:23])[CH3:24]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 1317297552-[6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamide

Produkt 1

HCID 1317297543-[6-[tert-butylsilyloxy(diphenyl)methyl]-2-methylimidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dioneAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Potassium tert-butoxide (1.0 M in THF, 1.90 ml, 1.90 mmol, 3.0 equiv) is added dropwise at room temperature under an atmosphere of argon to a solution of (1H-Indol-3-yl)-oxo-acetic acid methyl ester (192 mg, 0.93 mmol, 1.5 equiv) and of 2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamide (300 mg, 0.62 mmol) in anhydrous tetrahydrofuran (5.0 ml, dried over molecular sieves). The reaction mixture is stirred for 30 minutes at 0° C., 30 minutes at room temperature and 1 hour at 45° C. It is then diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. After three extractions with EtOAc, the combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue via flash chromatography (gradient of hexane/EtOAc 50:50 to 20:80) affords the title compound (180 mg, 45%). MS (ES+): 611 (M+H)+.

Aufarbeitung

  1. extractionAfter three extractions with EtOAc
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue via flash chromatography (gradient of hexane/EtOAc 50:50 to 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-2597014dcd6e4282958a78e49cdc96fb
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193236B2

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