Tetrabutylammonium Fluoride → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol

HRID 1515658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515658
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:40]([C:47]2[CH:52]=[CH:51][C:50]([S:53]([CH3:56])(=[O:55])=[O:54])=[CH:49][CH:48]=2)=[CH:41][CH:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:42]1([CH:41]=[C:40]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([O:19][CH2:20][CH2:21][OH:22])[CH:18]=[C:13]3[CH:12]=2)[C:47]2[CH:52]=[CH:51][C:50]([S:53]([CH3:56])(=[O:55])=[O:54])=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44][CH2:43]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 672286821-benzenesulfonyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 672286052-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanolAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-benzenesulfonyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (870 mg, 1.08 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 10 mL, 10 mmol) was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol (460 mg, quant.) as a white solid: LC/MS m/e calcd for C23H26N2O4S [M+H]+ 427.54, observed 427.4.

Aufarbeitung

  1. washwashed with a saturated aqueous ammonium chloride solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-513c756e908f4734bb7831912ba2bbbe
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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