* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
2-(1-cyclopropyl-1H-pyrazol-4-yl)-5-nitrobenzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate; triphenylphosphine; In propan-1-ol; water; at 100℃; for 3h;Inert atmosphere;
2-Chloro-5-nitrobenzenesulfonamide (674 mg, 2.85 mmol) and i-cyclopropyl-4-(4,4,5,5-tetramethyl-i,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.00 g, 4.27 mmol) were dissolved in npropanol (34 ml) and bis(triphenylphosphine)palladium(l I) dichioride (CAS 13965-03-2)(100 mg, 142 pmol) and triphenylphosphine (37.3 mg, 142 pmol) were added. Thereaction was purged with argon for 5 minutes and aq. potassium carbonate (5.7 ml, 1.0 M,5.7 mmol) was added. The reaction was heated at 100°C for 3h. Afterwards the mixturewas filtered over Celite and the solvent was removed under reduced pressure. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Whatmanfilter and the solvent was removed under reduced pressure.The crude was used in the next step without further purification.
5-amino-2-(1-cyclopropyl-1H-pyrazol-4-yl)-N-[(dimethylamino)methylidene]benzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2-Chloro-5-nitrobenzenesulfonamide (674 mg, 2.85 mmol) and 1 -cyclopropyl-4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole (1 .00 g, 4.27 mmol) were dissolved in n- propanol (34 ml) and bis(triphenylphosphine)palladium(ll) dichloride (CAS 13965-03-2) (100 mg, 142 muetaetaomicronIota) and triphenylphosphine (37.3 mg, 142 muetaetaomicronIota) were added. The reaction was purged with argon for 5 minutes and aq. potassium carbonate (5.7 ml, 1.0 M, 5.7 mmol) was added. The reaction was heated at 100°C for 3h. Afterwards the mixture was filtered over Celite and the solvent was removed under reduced pressure. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Whatmanfilter and the solvent was removed under reduced pressure. The crude was used in the next step without further purification. (0458) 2-(1 -Cyclopropyl-1 /-/-pyrazol-4-yl)-5-nitrobenzenesulfonamide (1.17 g, 3.79 mmol) and 1 ,1 -dimethoxy-/V,/V-dimethylmethanamine (1 .0 ml, 7.6 mmol) were dissolved in DMF (25 ml) and the reaction was stirred at room temperature until completion of the reaction. The solvent was removed under reduced pressure and the crude was used without further purification in the next step. (0459) 2-(1 -Cyclopropyl-1 /-/-pyrazol-4-yl)-/V-[(dimethylamino)methylidene]-5- nitrobenzenesulfonamide (1.84 g, 5.06 mmol) was dissolved in THF (30 ml) and the flask was flushed with nitrogen. Palladium on charcoal (10percent loading, 53.9 g, 506 muetaetaomicronIota) was added and the flask was evacuated and subsequently flushed with hydrogen (1 bar). Stirring was continued at room temperature until completion of the reaction. The reaction mixture was filtered over Celite and the solvent was removed under reduced pressure. The crude was used without further purification in the next step (1.3 g, 53percent purity, 75percent yield over 3 steps). (0460) LC-MS (Method A): Rt = 0.70 min; MS (ESIpos): m/z = 334 [M+H]+
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
