* 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.
With Pd/C (30%); hydrogen; In methanol; at 20.0℃; for 4.0h;
To a solution of <strong>[25369-31-7]7-nitroindolin-2-one</strong> in methanol (1.0 gm/60 ml), added Pd/C (300 mg, 30 wt %). H2 gas maintained with pressure using hydrogen gas balloon, solution stirred for 4 hours at RT. The catalyst was removed by filtration over celite. The filtrate was concentrated in vacuo to give crude product, which was washed with diethyl ether to afford compound 7-aminoindolin-2-one; YD: 76.77%; mp:248-251 C.; R1 0.6 (CHC13:MeOH:: 9.0:1.0). 1H NMR (DMSO-d6) 200 MHz, delta 3.382 (s, 2H), 4.794 (s, 2H), 6.453- 6.498 (m, 2H), 6.673 (t, J=8.0 Hz, 1H), 9.906 (s, 1H). MS (ESI): mlz 146.8 [M-H]-.
N-(2-oxo-2,3-dihydro-1H-indol-7-yl)thiophene-2-sulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
97%
With pyridine; at 0 - 20℃; for 2.0h;
Reference Example 9 N-(2-Oxo-2,3-dihydro-1H-indol-7-yl)thiophene-2-sulfonamide [Show Image] To a mixture of <strong>[25369-32-8]7-amino-2-oxo-2,3-dihydro-1H-indole</strong> (1.53 g) and pyridine (20 mL) was added thiophene-2-sulfonyl chloride (2.26 g) at 0C, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography, and eluted with ethyl acetate. The eluate was treated with activated carbon and concentrated to give the title compound (2.93 g, yield 97%) as colorless crystals. The crystals were recrystallized from tetrahydrofuran-hexane. melting point >230C (decomposition).
7-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With triethylamine;zinc(II) chloride; In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol; at 0 - 20℃;
<strong>[25369-32-8]7-amino-oxindole</strong> (910 mg, 6.1 mmol) was added portionwise to a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (1.33 g, 1 eq) and ZnCl2 (6.1 mL of a 1M solution in ether) in 1:1 DCE/t-butanol (30 mL) at 0 C. After 15 minutes a solution of Et3N (0.94 mL, 1.1 eq) in 1:1 DCE/t-butanol (10 mL) was added dropwise. The reaction was allowed to warm to RT overnight. The reaction was then concentrated and the product triturated from methanol as a green solid 1.61 g (81%). 1H NMR (DMSO-d6, 400 MHz) delta 3.51 (s, 2H), 6.92 (m, 1H), 7.08 (d, J=7.5 Hz, 2H), 8.66 (s, 1H), 10.10 (s, 1H), 10.17 (s, 1H); HPLC ret. time: 5.870 min. LRMS (M+) 329.1, 331.1.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2.0h;
To a suspension of 7-aminooxindole (32 mg, 0.22 mmol) in CH2Cl2 (1 mL) was added EDC (83 mg, 0.43 mmol) and formic acid (12 mg, 0.26 mmol). The reaction mixture was stirred at rt for 2 h and then filtered. The filter cake was washed with diethyl ether to give the title compound as a grey solid (27 mg, 71%). 1H NMR (400MHz, CD3OD) delta 8.23 (s, IH), 7.20 (d, IH, J= 8 Hz), 7.15 (d, IH, J= 8 Hz), 7.02 (t,IH, J= 8 Hz), 3.59 (s, 2H); MS ESI [M + H]+, calcd for [C9H8N2O2 +H]+ 177.07; found m/z 177.0.
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;
To a suspension of <strong>[25369-32-8]7-aminoindolin-2-one</strong> (60 mg, 0.41 mmol) in THF (3 mL) was added DIPEA (0.28 mL, 1.62 mmol), and 2-isocyanatopropane (0.05 mL, 0.49 mmol). The mixture was stirred at rt overnight then filtered. The filter cake was washed with diethyl ether to give the title compound as a pale solid (57.3 mg, 61%). 1H NMR (400 MHz, CD3OD) delta 7.09-7.04 (m, 2H), 6.99-6.95 (m, IH), 3.57 (s, 2H), 2.64 (m, IH), 1.20 (d, 6H, J = 6.4Hz). MS ESI [M + H]+, calcd for [Ci2H15N3O2 +H]+ 234.12; found m/z 234.0.
A 13 mg (0.0877 mmol) solution of 7-aminooxindole (T. Nakashima & I. Suzuki, Chem. Pharm. Bull. (1969) 11, 2293) and lH-indazole-6-carbaldehyde (14 mg, 0.0965 mmol) in MeOH (1.0 mL) was treated with piperidine (~1 uL, 0.00877 mmol) and the reaction was heated to 60 0C for 4 hours. The MeOH was then removed in vacuo and the residue treated with 95:5 CH2Cl2/Me0H. The resulting precipitate was filtered and washed with 95:5 CH2Cl2MeOH to obtain the title compound as a orange powder (6.7 mg, 28 %). 1H NMR (400 MHz, CD3OD) delta 8.14 (s, IH), 7.94-7.87 (m, 3H), 7.46 (d, J = 8.19 Hz, IH), 7.31 (d, J = 7.63 Hz, IH), 6.90 <n="134"/>(d, J = 7.89 Hz, IH), 6.81 (t, J = 7.79 Hz, IH); MS ESI 277.0 [M + H]+, calcd for [C16H12N4O + H]+ 277.11.
1-(4-fluorophenyl)-2-oxo-N-(2-oxoindolin-7-yl)-1,2-dihydropyridine-3-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 3.0h;
General procedure: Appropriate aminoindolin-2-one (1equiv) was added to a mixture of appropriate 3-amino-3-oxopropanoic acid/2-pyridone acid/4-pyridone acid (1equiv), TBTU (1.5equiv) and TEA (3equiv) in DMF/acetonitrile (1:3, 0.16M). The resulting reaction mixture was stirred at room temperature for 3h. Reaction mixture was then concentrated in vacuo. Title compound was collected as solid by filtration and dried.
General procedure: Oxalyl chloride (6.61mmol) was added dropwise into a stirred solution of the appropriate benzamide (2.6mmol) in CH2Cl2 (10mL). The mixtures were heated at reflux for 20-22h. Then, solvents were evaporated in vacuo to give the respective crude benzoyl isocyanates 4a-k, which were used immediately in the next step without purification. Aminoindolin-2-one (2.8mmol) was added into a stirred solution of the appropriate benzoyl isocyanate (2.8mmol) in acetonitrile (10mL). After addition, each mixture was heated at 70-80C for 2-3h. The solid products were each filtered, washed with acetonitrile, and air dried.
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