Water → 2-Aminocarbonylamino-5-(4-phenylethynylphenyl)pyrrole-3-carboxamide

HRID 1011580Notes

Reaction equation

HRID 1011580 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].C(=O)([O-])[O-].[Na+].[Na+].[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>[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.O1CCOCC1>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:33]#[C:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:15][CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10821PhenylacetyleneHCID 250057042-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide

Product 1

HCID 592859812-Aminocarbonylamino-5-(4-phenylethynylphenyl)pyrrole-3-carboxamideYield 57%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
95 °C

Procedure

2-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide (Compound No. 1-1, 100 mg, 0.31 mmol), sodium carbonate (69 mg, 0.65 mmol), copper(I) iodide (12 mg, 0.063 mmol), phenylacetylene (68 μL 0.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (38 mg, 0.033 mmol) in mixed solvent (8 mL), which consists of water and 1,4-dioxane (1:3), were stirred at 95° C. for 5 hours. The brine (5 mL) was added to the reaction solution, extracted with ethyl acetate (10 mL), and then the organic layer was dried over magnesium sulfate. The layer was filtered with celite and the solvent was removed under reduced pressure. The obtained solid was washed with ethyl acetate (2 mL), and dried under reduced pressure to give the target compound (61 mg) as a pale yellow solid (Yield 57%).

Workup

  1. extractionextracted with ethyl acetate (10 mL)
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationThe layer was filtered with celite
  4. customthe solvent was removed under reduced pressure
  5. washThe obtained solid was washed with ethyl acetate (2 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-22819068314e43739b7ead6b6e714acb
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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