Potassium Carbonate → N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

HRID 1960512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1960512
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]2[S:12][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][C:16]=4[NH:22][S:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)(=[O:25])=[O:24])=[N:10][CH2:9]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:37][CH:38]([F:40])I>CN(C)C=O.C(OCC)(=O)C>[F:37][CH:38]([F:40])[N:22]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[NH:14][C:13]([C:11]1[S:12][CH:8]([CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH2:9][N:10]=1)=[CH:21]2)[S:23]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:25]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2775155Difluoro(iodo)methaneHCID 59135769N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

Produkt 1

HCID 24899516N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamideAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (200 mg) in N,N-dimethylformamide (3 mL) were added potassium carbonate (90.0 mg) and difluoroiodomethane (77.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (60 mg, yield 27%) as white crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:513(MH+). melting point 185-186° C.

Aufarbeitung

  1. washwashed with water and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b2ca271f34db42afb2cf13e632fd6f5e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410087B2

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