Sodium Bicarbonate → HCID 67314786, compound

HRID 1011581Notes

Reaction equation

HRID 1011581 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].C(=O)([O-])O.[Na+].[CH:25]([Si:28]([C:35]#[CH:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>[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.O.O1CCOCC1>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:36]#[C:35][Si:28]([CH:25]([CH3:27])[CH3:26])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

9

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734682(Triisopropylsilyl)acetyleneHCID 59285953HCID 59285953, compound

Product 1

HCID 67314786HCID 67314786, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
95 °C

Procedure

2-Aminocarbonylamino-5-(3-bromophenyl)pyrrole-3-carboxamide (Compound No. 1-31, 200 mg, 0.62 mmol), sodium hydrogencarbonate (133 mg, 1.6 mmol), copper (I) iodide (16 mg, 0.084 mmol), (triisopropylsilyl)acetylene (0.28 mL, 1.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (38 mg, 0.033 mmol) in mixed solvent (12 mL), which consists of water and 1,4-dioxane (1:5), were stirred at 95° C. for 4.5 hours. The brine (5 mL) and water (5 mL) were added to the reaction solution, extracted with ethyl acetate (15 mL), and then the organic layer was dried over magnesium sulfate. The layer was filtered with celite, the solvent was removed under reduced pressure, and then the obtained solid was washed with diethyl ether (2 mL) to give the intermediate 2-aminocarbonylamino-5-(3-triisopropylsilylethynylphenyl)pyrrole-3-carboxamide as a yellow solid. Moreover, 1.0M tetrabutylammonium fluoride in tetrahydrofuran solution (0.48 mL, 0.48 mmol) was added to a solution of this intermediate in tetrahydrofuran (5 mL) and the mixture was stirred at 75° C. for 3.5 hours. The reaction solution was concentrated in vacuo, the obtained residue was purified by silica gel column chromatography to give the target compound (47 mg) as a colorless solid (Yield 29%).

Workup

  1. extractionextracted with ethyl acetate (15 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 diethyl ether (2 mL)

Sources & evidence

ORD record
ord-d40ed38c0e5f4328b7168b3271b15bf1
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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