Triethylamine → N-(5-Nitro-2-(phenylethynyl)phenyl)butyramide

HRID 1886955Notes

Reaction equation

HRID 1886955 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])(=O)=O.C(N(CC)CC)C.[C:31]1([C:37]#[CH:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[NH4+]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([C:38]#[C:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:8]([NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:9]=1)([O-:15])=[O:14]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 25517Ammonium ChlorideHCID 112912342-Butyramido-4-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 11358741N-(5-Nitro-2-(phenylethynyl)phenyl)butyramideYield 78%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (860 mg, 2.42 mmol) in dry acetonitrile (30 mL) under nitrogen was added tetrabutylammonium iodide (1.34 g, 3.62 mmol), tetrakis(triphenylphosphine)palladium(0) (280 mg, 0.24 mmol) and copper iodide (140 mg, 0.72 mmol). Triethylamine (6 mL) was then added, followed by phenyl acetylene (530 μL, 4.83 mmol). The resulting solution was stirred at room temperature for 2 h. Ammonium chloride was then added to quench the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (hexanes to ethyl acetate) to afford 580 mg (78%) of the title compound.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customevaporated
  7. customThe resulting solid was purified by column chromatography
  8. washeluting

Sources & evidence

ORD record
ord-a4641c20fdba4c488ad1ba27e0c9b276
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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