Phenylacetylene → HCID 59189857, compound

HRID 216629Notes

Reaction equation

HRID 216629 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:3].C(=O)([O-])[O-].[K+].[K+].[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.O1CCOCC1.[Cl-].[Na+].O.[Cu]I.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>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][CH:10]=[C:9]([C:31]#[C:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]=2)=[O:3]

Participants

8

Reactant 3

HCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 24987222HCID 24987222, compound2×

Product 1

HCID 59189857HCID 59189857, compoundYield 42.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

A solution mixture of 2-aminocarbonylamino-6-bromoindole-3-carboxamide (Compound 3-1, 50 mg, 0.17 mmol), potassium carbonate (36 mg, 0.26 mmol), copper (I) iodide (3.0 mg, 0.017 mmol), phenylacetylene (22 μL, 0.20 mmol) and tetrakis(triphenylphosphine)palladium (0) (20 mg, 0.017 mmol) in water-1,4-dioxane (1:3, 5 mL) was stirred at 100° C. for 3.5 hours. Brine (5 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous magnesium sulfate and was filtered throught Celite® pad. After the solvent was evaporated under reduced pressure, the resultant solid was washed with a solution mixture of ethanol and chloroform (ethanol/chloroform=1/2, 3 mL), and dried under reduced pressure to give the title compound (23 mg) as a slightly brown solid (yield 43%).

Workup

  1. extractionthe whole was extracted with ethyl acetate (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customAfter the solvent was evaporated under reduced pressure
  5. washthe resultant solid was washed with a solution mixture of ethanol and chloroform (ethanol/chloroform=1/2, 3 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-bd702fabfb4a48e0b17ed6cb509622cf
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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