6-Chloro-4-iodopyridin-3-amine → 6-Chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amine

HRID 1044012

Reaktionsgleichung

Reaktionsgleichung von HRID 1044012
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[C:10]([C:12]1([CH3:15])[CH2:14][CH2:13]1)#[CH:11]>CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:11]#[C:10][C:12]2([CH3:15])[CH2:14][CH2:13]2)[CH:3]=1

Komponenten

6

Edukt 2

HCID 184070406-Chloro-4-iodopyridin-3-amineHCID 215905601-Ethynyl-1-methylcyclopropane

Produkt 1

HCID 579081926-Chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-4-iodopyridin-3-amine (7.0 g, 28 mmol) in Et3N (100 mL) was added 1-ethynyl-1-methyl-cyclopropane (11.0 g, 137 mmol), CuI (0.53 g, 2.8 mmol) and Pd(PPh3)2Cl2 (1.9 g, 2.8 mmol) under N2 atmosphere. The mixture was refluxed overnight and quenched with H2O (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and purified by chromatography on silica gel (3% EtOAc in Petroleum ether as eluant) to afford 6-chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amine (3.0 g, 53%). 1H-NMR (CDCl3, 300 MHz) δ 7.84 (s, 1H), 7.08 (s, 1H), 4.11 (br s, 2H), 1.37 (s, 3H), 1.03 (t, J=2.4, 2H) 0.76 (t, J=2.4, 2H).

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. customquenched with H2O (100 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. custompurified by chromatography on silica gel (3% EtOAc in Petroleum ether as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-f3f87881eed3484082014f791528b3ae
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563573B2

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