2-Chloro-5-methylpyridin-3-amine → (2-Chloro-5-methyl-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-pyridin-4-yl-ethylidene]-amine

HRID 659935Notes

Reaction equation

HRID 659935 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:19]=[C:20]([NH2:25])[C:21]([Cl:24])=[N:22][CH:23]=1.O.C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:24][C:21]1[C:20]([N:25]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:19][C:18]([CH3:17])=[CH:23][N:22]=1

Participants

7

Reactant 4

HCID 27344222-Chloro-5-methylpyridin-3-amineHCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanoneHCID 21226206Ethyl acetate hexaneHCID 22272177Toluene water

Product 1

HCID 86643497(2-Chloro-5-methyl-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-pyridin-4-yl-ethylidene]-amineYield 64%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid (500 mg), 2-(4-fluorophenyl)-1-(pyridine-4-yl)ethanone (10 g, 46 mmoles) and 5-methyl-3-amino-2-chloropyridine (8.6 g, 60 mmoles) in 350 mL of toluene was refluxed overnight with a Dean-Stark removal of water/toluene azeotrope. The reaction mixture was further concentrated, the brown residue suspended in an ethyl acetate/hexane mixture (9/1) and filtered. The solid was solubilised in ethyl acetate and purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 10 g of (2-Chloro-5-methyl-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-pyridin-4-yl-ethylidene]-amine as a brown solid.

Workup

  1. filtrationfiltered
  2. custompurified by chromatography on silica gel (ethylacetate/hexane 1/1)

Sources & evidence

ORD record
ord-cebb7a9f02cb41b2aa42c3beb01ab0fd
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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