Sodium Bicarbonate → HCID 67314786, compound

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence