Chloride → 1-(2-(Phenylethynyl)pyridin-3-yl)ethanone

HRID 1496856Notes

Reaction equation

HRID 1496856 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]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.[Cl-]>CN(C=O)C.C(Cl)Cl>[C:11]1([C:17]#[C:18][C:5]2[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 99903691-(2-Bromopyridin-3-yl)ethan-1-one

Product 1

HCID 147130351-(2-(Phenylethynyl)pyridin-3-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Step 1 (=Reaction 1): 66 mg 3-Acetyl-2-bromopyridine, 56 μL phenylacetylene, 170 μL DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25° C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g SiO2, cyclohexane→cyclohexane/ethylacetate 70:30) to yield 40 mg 1-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E), M+H=222.

Workup

  1. customStep 1 (=Reaction 1)
  2. extractionextracted with diluted aq. NH3 and brine
  3. concentrationThe organic phase was concentrated
  4. customthe mixture separated via flash chromatography (10 g SiO2, cyclohexane→cyclohexane/ethylacetate 70:30)

Sources & evidence

ORD record
ord-213568a28fd24d53bf70198d87925ae2
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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