3-Ethynylpyridine → 4-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine

HRID 593564Notes

Reaction equation

HRID 593564 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[F:9][C:10]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13](I)[C:11]=1[NH2:12]>C(N(CC)CC)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.[Cu]I>[Cl:17][C:15]1[CH:14]=[C:13]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[C:11]([NH2:12])=[C:10]([F:9])[CH:16]=1

Participants

6

Reactant 2

HCID 1860033-EthynylpyridineHCID 27736504-Chloro-2-fluoro-6-iodoaniline

Product 1

HCID 582155984-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of 3-ethynylpyridine (1.13 g, 11 mmol) and 2-fluoro-4-chloro-6-iodoaniline (2.71 g, 10 mmol) in triethylamine (100 mL) is added PdCl2(PPh3)2 (175 mg, 0.25 mmol) and CuI (95 mg, 0.50 mmol) and the mixture is refluxed for 1 h. The solvent is removed in vacuo and the residue is purified by silica gel flash chromatography (dichloromethane-methanol, 1:0 to 24:1) to give 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine. MS (ESI) m/z 247 (M+H)+.

Workup

  1. temperaturethe mixture is refluxed for 1 h
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by silica gel flash chromatography (dichloromethane-methanol, 1:0 to 24:1)

Sources & evidence

ORD record
ord-dc15832643bd49ac96a2a1f259f4d5b0
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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