Chloride → 1-(2-(Pyridin-2-ylethynyl)pyridin-3-yl)ethanone

HRID 1402707Notes

Reaction equation

HRID 1402707 reaction equation
[C:1]([C:4]1[C:5](Br)=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)#[CH:12].C(N(CC)CC)C.[Cl-]>CN(C=O)C.C(Cl)Cl>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]#[C:12][C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 137268EthynylpyridineHCID 99903691-(2-Bromopyridin-3-yl)ethan-1-one

Product 1

HCID 712383301-(2-(Pyridin-2-ylethynyl)pyridin-3-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

750 mg 3-Acetyl-2-bromopyridin, 550 μL 2-ethynyl-pyridine, 765 μL triethylamin, 255 mg triphenylphosphinpalladium(II) chlorid, 17 mg Cu(I)I were suspended in 10 mL DMF under argon atmosphere and stirred for 2 h at 25° C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and saturated NH4Cl solution. The organic phase was concentrated and the mixture separated via FCC (100 g SiO2, cyclohexane→cyclohexane/ethylacetate 35:65) to yield 455 mg 1-(2-(pyridin-2-ylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=0.88 min (method E) M+H=223.

Workup

  1. extractionextracted with diluted aq. NH3 and saturated NH4Cl solution
  2. concentrationThe organic phase was concentrated
  3. customthe mixture separated via FCC (100 g SiO2, cyclohexane→cyclohexane/ethylacetate 35:65)

Sources & evidence

ORD record
ord-0e60fbdeb892424081bbd0e76f74e87a
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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