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Dimethylformamide → 3-Chloro-5-[2-(4-methoxy-2-methylphenyl)ethynyl]-2-pyridinecarbonitrile

HRID 2167637
Notes
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Reaction equation

HRID 2167637 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11])#[CH:2].[Cl:12][C:13]1[C:14]([C:20]#[N:21])=[N:15][CH:16]=[C:17](Cl)[CH:18]=1.C(N(CC)CC)C.CN(C=O)C>[Cu]I.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.CCOC(C)=O>[Cl:12][C:13]1[C:14]([C:20]#[N:21])=[N:15][CH:16]=[C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=2[CH3:11])[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27696993,5-Dichloro-2-cyanopyridineHCID 162137961-Ethynyl-4-methoxy-2-methylbenzene

Product 1

HCID 581665223-Chloro-5-[2-(4-methoxy-2-methylphenyl)ethynyl]-2-pyridinecarbonitrile

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a round bottom flask capped with septa was added 1-ethynyl-4-methoxy-2-methylbenzene (commercially available, 1.1 equiv.), 3,5-dichloropicolinonitrile (commercially available, 1 equiv.), triethylamine (5 equiv.), and anhydrous DMF (0.2 M). Vacuumed and nitrogen flushed for three times. CuI (0.05 equiv.) and bis(triphenylphosphine)dichloro-palladium(II) (0.05 equiv.) were added. The septum was replaced with a refluxing condenser and the flask was heated at 60° C. overnight under nitrogen atmosphere. Upon completion of the reaction as monitored by TLC, the content of the flask was loaded onto a large silica gel column pretreated with hexanes. Flash chromatography (silica gel, hexanes:EtOAc (1:4%)) afforded 3-chloro-5-((4-methoxy-2-methylphenyl)ethynyl)picolinonitrile.

Workup

  1. customTo a round bottom flask capped with septa
  2. customVacuumed and nitrogen flushed for three times
  3. customThe septum was replaced with a refluxing condenser
  4. customUpon completion of the reaction

Sources & evidence

ORD record
ord-3373d74ab08c402592b083f3df1664ba
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045470B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes