Water → 2-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 351104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351104
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([NH:13]S(C)(=O)=O)=[C:5](I)[CH:4]=1)#[N:2].[C:19]([Si:23]([O:26][C:27]([CH3:31])([CH3:30])[C:28]#[CH:29])([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].CCN(CC)CC.O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:19]([Si:23]([CH3:25])([CH3:24])[O:26][C:27]([C:28]1[NH:13][C:6]2[C:5]([CH:29]=1)=[CH:4][C:3]([C:1]#[N:2])=[C:8]([C:9]([F:12])([F:11])[F:10])[CH:7]=2)([CH3:30])[CH3:31])([CH3:22])([CH3:21])[CH3:20]

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 11084826Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-HCID 21091191N-(4-Cyano-2-iodo-5-(trifluoromethyl)phenyl)methanesulfonamide

Produkt 1

HCID 210911842-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrileAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-(4-Cyano-2-iodo-5-trifluoromethyl-phenyl)-methanesulfonamide (1.95 g, 5.0 mmol), tert-Butyl-(1,1-dimethyl-prop-2-ynyloxy)-dimethyl-silane (992 mg, 5.0 mmol), PdCl2(PPh3)2, (175 mg, 0.25 mmol), CuI (95 mg, 0.5 mmol), NEt3 (1.4 mL, 10.0 mmol), was mixed in DMF (15 mL) and stirred at room temperature for 16 hours. Water was added and the mixture was extracted twice with ethyl acetate. The organic layers were washed with 10% LiCl solution, dried over magnesium sulfate, filtered, evaporated to a brown oil. The brown oil was purified by column chromatography eluting with 1, 3, and 10% ethyl acetate/hexanes. The product was obtained as a white solid (306 mg, 16%). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.92 S, 1H), 7.67 (s, 1H), 6.27 (d, J=1.2 Hz, 1H), 1.58 (s, 6H), 0.85 (s, 9H), 0.3 (s, 6H). MS (m/z): 405 (MNa+), 381 (MH−).

Aufarbeitung

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layers were washed with 10% LiCl solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to a brown oil
  6. customThe brown oil was purified by column chromatography
  7. washeluting with 1, 3, and 10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bf522c38f7ab4b769fbb75a1a8b8485b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183309B2

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