Potassium tert-butoxide → 5-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine

HRID 1044013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044013
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2([CH3:14])[CH2:13][CH2:12]2)[CH:3]=1.CC([O-])(C)C.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:9]=[C:10]([C:11]3([CH3:14])[CH2:13][CH2:12]3)[NH:8][C:5]2=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 579081926-Chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amine

Produkt 1

HCID 579081755-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amine (3.0 g, 15 mmol) in DMF (50 mL) was added t-BuOK (3.3 g, 29 mmol) under N2 atmosphere. The mixture was heated at 80° C. overnight and quenched with H2O (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and purified by chromatography on silica gel (3% EtOAc in petroleum ether) to afford 5-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine (2.2 g, 73%). 1H-NMR (CDCl3, 300 MHz) δ 9.79 (br s, 1H), 8.37 (s, 1H), 7.36 (s, 1H), 6.16 (s, 1H), 1.51 (s, 3H), 1.09 (m, 2H), 0.89 (m, 2H).

Aufarbeitung

  1. customquenched with H2O (100 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 mL×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by chromatography on silica gel (3% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c5723815144547c3a710d8476f6c9db9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563573B2

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