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Dimethylformamide → HCID 178474488, compound

HRID 588615
Notes
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Reaction equation

HRID 588615 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12](I)=[C:11]([NH:14][C:15](=[O:17])[CH3:16])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.CN(C=O)C>C(OCC)(=O)C.O.[Cu](I)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>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:25]#[C:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:11]([NH:14][C:15](=[O:17])[CH3:16])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 178474489HCID 178474489, compound

Product 1

HCID 178474488HCID 178474488, compoundYield 28.5%

Reagents, catalysts & solvents 4

HCID 83717
Copper iodide
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Nitrogen was bubbled through a mixture of N-[3-(3-fluorophenyl)-4-iodo-1H-pyrazol-5-yl]acetamide (10.8 g, 44 mmol), phenyl acetylene (12.5 g, 123 mmol), triethylamine (100 mL) and DMF (40 mL) for 15 min. Copper iodide (840 mg, 4.42 mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.5 g, 2.1 mmol) were added and the reaction mixture was stirred at 90° C. under nitrogen for 6 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 1:0 to 0:1) yielding the title compound as a solid (4 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 1:0 to 0:1)

Sources & evidence

ORD record
ord-4fa10f26029a42d3ac3009b40fc9f13e
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09227976B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes