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5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine → 2-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661545
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.C([Li])(C)(C)C.[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][CH2:35][C:34]1([CH:41]=[O:42])[CH2:38][CH2:39][CH3:40])=[O:32])([CH3:29])([CH3:28])[CH3:27]>CCOCC>[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][CH2:35][C:34]1([CH:41]([OH:42])[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1)[CH2:38][CH2:39][CH3:40])=[O:32])([CH3:28])([CH3:29])[CH3:27]
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Komponenten

5

Edukt 3

HCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 866208602-Formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 666875152-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5-bromo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (0.587 g, 1.66 mmol) in ether (20 mL) at −78° C. and under nitrogen was added tert-butyllithium (2.30 mL of 1.51 M solution in pentanes, 3.49 mmol) dropwise. After 90 minutes, a solution of 2-formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.400 g, 1.66 mmol) in ether (1 mL) was added to the reaction mixture dropwise. After stirring for one hour, the reaction mixture was warmed to ambient temperature over 30 minutes. The reaction mixture was quenched by the addition of saturated aqueous NH4Cl (20 mL) then extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (0.90 g). Purification by chromatography (silica, 5-20% EtOAc in hexanes) gave 2-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.576 g, 1.12 mmol, 53%) as a colourless gum.

Aufarbeitung

  1. customThe reaction mixture was quenched by the addition of saturated aqueous NH4Cl (20 mL)
  2. extractionthen extracted with EtOAc
  3. washThe combined extracts were washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow oil (0.90 g)
  7. customPurification by chromatography (silica, 5-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-17ea5a3024e04f2fa044861d6156a713
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084623B2

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