Water → 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine

HRID 1529211Notes

Reaction equation

HRID 1529211 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1I.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][N:13]=1.C(N(CC)CC)C.O>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]([CH2:8][CH3:9])[C:3]=1[C:19]#[C:18][C:15]1[CH:16]=[CH:17][C:12]([NH2:11])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 582353314-Chloro-2-ethyl-3-iodo-pyridine

Product 1

HCID 582353135-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP1 starting from 1.0 g (3.7 mmol) 4-chloro-3-iodo-2-ethyl-pyridine and 485 mg (4.1 mmol) 2-amino-5-ethynyl-pyridine using 36 mg (0.40 mmol) CuI, 131 mg (0.40 mmol) PdCl2(PPh3)2 and 5.2 mL (39.5 mmol) triethylamine in 25 mL dry DMF. After completion of the reaction the reaction mixture is added dropwise into water. The precipitate is filtered off and taken up with iPrOH. The product remains is solution while the side-product (alkyne dimer from Glaser-homo-coupling) forms a precipitate and is filtered off. The mother liquid is concentrated under vacuum. Yield: 718 mg (75%).

Workup

  1. customAfter completion of the reaction the reaction mixture
  2. filtrationThe precipitate is filtered off
  3. filtrationis filtered off
  4. concentrationThe mother liquid is concentrated under vacuum

Sources & evidence

ORD record
ord-5b2d5b788c4e4c66b13202652b5c3cb6
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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