Potassium Carbonate → methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate

HRID 1713944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713944
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[CH:26]=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].S([CH2:44][N+:45]#[C-:46])(C1C=CC(C)=CC=1)(=O)=O>CO.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:24])[CH3:25])=[O:22])[C:8]=2[C:26]2[O:27][CH:46]=[N:45][CH:44]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86623944methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-formyl-1H-indole-6-carboxylate

Produkt 1

HCID 68437594methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-formyl-1H-indole-6-carboxylate (from Step 4) in MeOH (0.05 M) was added K2CO3 (1.05 eq.) and tosylmethyl isocyanide (1.05 eq.). The resulting solution was refluxed under nitrogen for 1.5 h. The mixture was diluted with EtOAc and the organic phase was extracted with HCl (1N) and brine. The organic phase was then dried over Na2SO4 and evaporated in vacuo to give the clean product (quantitative).

Aufarbeitung

  1. temperatureThe resulting solution was refluxed under nitrogen for 1.5 h
  2. extractionthe organic phase was extracted with HCl (1N) and brine
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. customevaporated in vacuo
  5. customto give the clean product (quantitative)

Quellen und Nachweise

ORD-Eintrag
ord-588884e0ebc6469592a3cdd257e10ee7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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