Nitrogen → 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine

HRID 1043996

Reaktionsgleichung

Reaktionsgleichung von HRID 1043996
[Cl:1][C:2]1[N:7]=[C:6](I)[C:5]([NH2:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[CH:20].N#N>C1(C)C=CC=CC=1.O.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.[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]([C:20]#[C:19][C:18]([CH3:22])([CH3:21])[CH3:17])[C:5]([NH2:9])=[CH:4][CH:3]=1

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 184070436-Chloro-2-iodopyridin-3-amine

Produkt 1

HCID 579081596-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 6-chloro-2-iodo-pyridin-3-ylamine (16.0 g, 62.7 mmol) in toluene (160 mL) and water (80 mL) were added Et3N (12.7 g, 125 mmol), Pd(PPh3)2Cl2 (2.2 g, 3.1 mmol), CuI (238 mg, 1.3 mmol) and 3,3-dimethyl-but-1-yne (7.7 g, 94 mmol) successively under N2 atmosphere. The reaction mixture was heated at 70° C. for 3 hours and was allowed to cool to room temperature. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 88%), which was used in the next step without further purification.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (150 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ce95d5be0f64daabb428b225b225bce
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563573B2

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