Hexane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

HRID 1515704

Reaktionsgleichung

Reaktionsgleichung von HRID 1515704
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([Li])[CH2:21][CH2:22][CH3:23].[CH3:25][CH2:26][CH2:27]CCC.C1(C=[O:37])CCCC1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:20]([OH:37])[CH2:21][CH:22]2[CH2:23][CH2:27][CH2:26][CH2:25]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 242292371-Benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Produkt 1

HCID 672295941-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanolAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (10.9 g, 39.5 mmol) in dry tetrahydrofuran (200 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 23 mL, 55.3 mmol) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (8 g, 71.1 mmol) dropwise. The mixture was stirred at −78° C. for 1 h and quenched with brine. The resulting mixture was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol as a white solid (12.5 g, 81.5%): LC/MS m/e calcd for C20H21FN2O3S [M+H]+ 389.46, observed 388.9.

Aufarbeitung

  1. stirringThe mixture was stirred at −78° C. for 1 h
  2. customquenched with brine
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-883c9bed3d3d4185b25f6889d85756a2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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