Carbon Dioxide → 2-((tert-Butyldimethylsilyloxy)methyl)-1-methyl-1H-indole-5-carboxylic acid

HRID 1481751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481751
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:5]2.[Li]CCCC.[C:26](=[O:28])=[O:27]>C1COCC1>[Si:14]([O:13][CH2:12][C:6]1[N:7]([CH3:11])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([C:26]([OH:28])=[O:27])=[CH:10][CH:9]=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 712845855-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indoleHCID 178418339Butyllithium

Produkt 1

HCID 712850522-((tert-Butyldimethylsilyloxy)methyl)-1-methyl-1H-indole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole (5.32 g, 15.0 mmol), prepared according to procedure described in Example 39, Step 3, in THF (30 mL) was added n-BuLi (2.5 M solution in hexanes, 7.30 mL, 18.25 mmol, 1.2 eq) at −78° C. dropwise. The mixture was stirred for 30 min at −78° C. before dry CO2 (g) was bubbled into reaction for 10 min. The reaction was quenched with saturated aqueous NH4Cl then extracted by CH2Cl2 (3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated under reduced pressure to give the title compound (4.80 g, ca. 15.0 mmol) in quantitative yield. The acid was carried over to next step without further purification.

Aufarbeitung

  1. customwas bubbled into reaction for 10 min
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionthen extracted by CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1a85251999fd460db08b0ffa853b9fee
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409905B2

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