Cesium carbonate → Ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1-(tetrahydro-2-furanylmethyl)-1H-indole-2-carboxylate

HRID 1006249

Reaktionsgleichung

Reaktionsgleichung von HRID 1006249
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH:38]1[CH2:42][CH2:41][CH2:40][O:39]1>CN(C)C=O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:37][CH:38]1[CH2:42][CH2:41][CH2:40][O:39]1)[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 22676745ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1H-indole-2-carboxylate

Produkt 1

HCID 22676841Ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1-(tetrahydro-2-furanylmethyl)-1H-indole-2-carboxylateAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1H-indole-2-carboxylate 220 (40.7 mg, 0.100 mmol) in N,N-dimethylformamide (0.9 mL) was added to a stirred mixture of cesium carbonate (325 mg, 1.00 mmol) and 2-(bromomethyl)tetrahydrofuran (19.8 mg, 0.120 mmol) in N,N-dimethylformamide (2.4 mL). The reaction was stirred for 16 h and then the mixture was filtered though a plug (500 mg) of silica gel using ethyl acetate to rinse. The filtrate was concentrated in vacuo and then reverse phase preparative HPLC chromatography gave 19.8 mg of product (retention time=2.4 min.). This material was taken to the next reaction without further purification or analysis.

Aufarbeitung

  1. filtrationthe mixture was filtered though a plug (500 mg) of silica gel
  2. washto rinse
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-731844116c9541c0b2d22f19a11c0e2e
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787651B2

Verknüpfte Notizen

Wird geladen…