Triethylamine → 5-(4-Chloro-2-methyl-pyridin-3-ylethynyl)-pyridin-2-ylamine

HRID 1529209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529209
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1I.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[CH:18])=[CH:13][N:12]=1.C(N(CC)CC)C>CN(C=O)C.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[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[C:18]#[C:17][C:14]1[CH:15]=[CH:16][C:11]([NH2:10])=[N:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 589309514-Chloro-3-iodo-2-methylpyridine

Produkt 1

HCID 582352785-(4-Chloro-2-methyl-pyridin-3-ylethynyl)-pyridin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The title compound is synthesized according to general procedure GP1 starting from 1.0 g (4.0 mmol) 4-chloro-3-iodo-2-methyl-pyridine and 513 mg (4.3 mmol) 2-amino-5-ethynyl-pyridine using 75 mg (0.40 mmol) CuI, 276 mg (0.40 mmol) PdCl2(PPh3)2 and 5.4 mL (39.5 mmol) triethylamine in 40 mL dry DMF. After completion of the reaction the solvent is removed under vacuum and the product is purified by chromatography on silica gel using a DCM/MeOH gradient (100:0 to 90:10). Yield: 617 mg (64%).

Aufarbeitung

  1. customAfter completion of the reaction the solvent
  2. customis removed under vacuum
  3. customthe product is purified by chromatography on silica gel using a DCM/MeOH gradient (100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-4e301ee3395e456eabd755fb4b50f457
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090564B2

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