2-Chloro-3-pyridylamine → HCID 73088680, compound

HRID 1017652Notes

Reaction equation

HRID 1017652 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.[NH2:17][C:18]1[C:19]([Cl:24])=[N:20][CH:21]=[CH:22][CH:23]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.O>C1(C)C=CC=CC=1>[Cl:24][C:19]1[C:18]([NH:17][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 805282-Chloro-3-pyridylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanoneHCID 22272177Toluene water

Product 1

HCID 73088680HCID 73088680, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-1-(pyridin-4-yl)ethanone (5.20 g, 24 mmol) and 3-amino-2-chloropyridine (4.04 g, 31.4 mmol) in toluene (150 ml) was added p-toluenesulfonic acid monohydrate (457 mg. 2.4 mmol) and the reaction mixture was brought to reflux with Dean-Stark removal of the toluene/water azeotrope. After 24 h, toluene was removed in vacuo and the residue was resuspended in ethyl acetate. The precipitate was collected by vacuum filtration to give (2-chloropyridin-3-yl)-[2-(4-fluorophenyl)-1-(pyridin-4-yl)-vinyl]amine (5.0 g) as a tan solid. The filtrate was concentrated in vacuo and purified by flash column chromatography (50%-80% ethyl acetate:hexanes gradient) to give additional 1.50 g of product.

Workup

  1. customtoluene was removed in vacuo
  2. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-e999f75cd32948e89c6e5319467ceca4
Source dataset
uspto-grants-2002_11
Patent number
US06479507B2

Reaction notes

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