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Triethylsilane → [3-(2-Benzenesulfonyl-pyridin-3-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid ethyl ester

HRID 1043406
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1043406
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:16])[CH3:2].[C:18]1([S:24]([C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][N:34]=2)C=O)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)[CH3:36].C([SiH](CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH2:36][C:28]2[C:27]([S:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:25])=[O:26])=[N:34][CH:33]=[CH:32][CH:29]=2)=[C:7]1[CH3:16])[CH3:2]
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Komponenten

6

Edukt 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 44185546Ethyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 866328282-(Benzenesulfonyl)isonicotinaldehyde

Produkt 1

HCID 59380589[3-(2-Benzenesulfonyl-pyridin-3-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid ethyl esterAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of (5-fluoro-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.95 g, 4.04 mmol), prepared as described in Example 1 of WO/2006/092579, and 2-(benzenesulfonyl)isonicotinaldehyde (1.0 g, 4.04 mmol) in dry dichloromethane (45 ml) was added slowly over 5 minutes to a stirred solution of TMSOTf (1.46 ml, 8.08 mmol) in dry dichloromethane (12.5 ml) cooled to 0° C. under N2. This mixture was stirred for 15 minutes and triethylsilane (1.94 ml, 12.12 mmol) was added in one portion. The reaction mixture was stirred for 2 h 30 minutes, warmed to room temperature, and quenched by the slow addition of saturated aqueous NaHCO3 (10 ml). The resulting biphasic mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate:hexanes 0:100 to 60:40 v/v to afford 1.21 g (64%) of the title compound (LCMS RT=6.63 min, MH+ 466.8).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 2 h 30 minutes
  2. temperaturewarmed to room temperature
  3. customquenched by the slow addition of saturated aqueous NaHCO3 (10 ml)
  4. extractionThe resulting biphasic mixture was extracted with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting solid was purified by column chromatography
  10. washeluting with ethyl acetate:hexanes 0:100 to 60:40 v/v

Quellen und Nachweise

ORD-Eintrag
ord-34f386ac938940ef8e74872f19af52d0
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563536B2

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