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2-Chloro-5-iodopyridin-4-amine → 5-(4-Amino-6-chloro-pyridin-3-ylethynyl)-nicotinic acid methyl ester

HRID 1897801
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1897801
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([C:19]#[CH:20])[CH:16]=[N:15][CH:14]=1>[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.C(N(CC)CC)C>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([C:19]#[C:20][C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][C:6]=2[NH2:8])[CH:16]=[N:15][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 454803662-Chloro-5-iodopyridin-4-amineHCID 53898384Methyl 5-ethynylnicotinate

Produkt 1

HCID 595784295-(4-Amino-6-chloro-pyridin-3-ylethynyl)-nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 250 mL round bottom flask flushed with N2 was charged with 2-chloro-5-iodo-pyridin-4-ylamine (1.00 g, 3.93 mmol), 5-ethynyl-nicotinic acid methyl ester (0.633 g, 3.93 mmol), copper(I) iodide (0.037 g, 0.196 mmol), bis(triphenylphosphine)palladium(II) chloride (0.138 g, 0.196 mmol) and triethyl amine (50 mL). The reaction mixture was stirred at 100° C. for 3 h. The reaction was cooled to room temperature, filtered and the precipitate washed thoroughly with ethyl acetate. The filtrate was washed with water twice. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford crude product 5-(4-amino-6-chloro-pyridin-3-ylethynyl)-nicotinic acid methyl ester as a brown solid which was taken onto next step without any purification. ESI-MS: m/z 288.0 (M+H)+

Aufarbeitung

  1. customA 250 mL round bottom flask flushed with N2
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe precipitate washed thoroughly with ethyl acetate
  5. washThe filtrate was washed with water twice
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9eeb1f981be048809cab03faaa19b75b
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519142B2

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