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CAS No. : | 129487-99-6 | MDL No. : | MFCD11617234 |
Formula : | C13H16N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 264.28 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen In methanol; ethyl acetate | 1.1-2 To a stirred solution of 1-Boc-6-nitroindoline (3.5 g, 13.2 mmol) in MeOH/EtOAc (80 ml_/40 ml_) was added 10% Pd/C (700 mg). The reaction was stirred under H2 (1 atm) overnight. The mixture was filtered through celite and concentrated to give 1 A (3.1 g, 100%). |
100% | With iron(III) chloride; N,N-Dimethylhydrazine In methanol for 4h; Heating / reflux; | 2.A The residue was dissolved in MeOH (4 mL), and FeCl3.6H2O (7 mg), Me2NNH2 (21 mmol), and charcoal (50 mg) were added. The resulting mixture was heated at reflux for 4 h. The mixture was filtered through diatomaceous earth and the filtrate was concentrated to obtain the desired compound in quantitative yield. |
94% | With palladium 10% on activated carbon; hydrogen In methanol for 2h; | Tert-butyl 6-aminoindoline-l-carboxylate(ll) A mixture of tert-butyl 6-nitroindoline- 1-carboxylate (b) (2.4 g, 9.1 mmol) and 10% Pd-C (0.1 g) in MeOH (10 mL) is stirred under 1 atmosphere pressure of hydrogen for 2 h. The mixture is filtered and concentrated. Silica gel column chromatography provided tert-butyl 6-aminoindoline-l-carboxylate (11) as a solid (2 g, 94%). MS m/z 235[M+H]+. |
With hydrogen | ||
With hydrogen In ethyl acetate at 17 - 25℃; for 5h; | 13 A mixture of a portion (2.64 g) of the material so obtained, 10% palladium-on-carbon catalyst (0.5 g) and ethyl acetate (200 ml) was stirred under 2.7 atmospheres pressure of hydrogen for 5 hours. The resultant mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60°C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-aminoindoline-l-carboxylate (1.5 g). 1H NMR: (CDCl3) 2.95 (m, 2H), 3.9 (m, 2H), 6.3 (d, IH), 6.9 (d, IH), 7.25 (s, IH). | |
With hydrogen In ethyl acetate for 5h; | 5 A mixture of a portion (2.64 g) of the material so obtained, 10% palladium-on-carbon catalyst (0.5 g) and ethyl acetate (200 ml) was stirred under 2.7 atmospheres pressure of hydrogen for 5 hours. The resultant mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-600C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-aminoindoline-l-carboxylate (1.5 g). 1H NMR: (CDCl3) 2.95 (m, 2H), 3.9 (m, 2H), 6.3 (d, IH), 6.9 (d, IH), 7.25 (s, IH). | |
With hydrogen In ethyl acetate at 23℃; for 6h; | ||
Stage #1: 6-nitro-2,3-dihydroindole-1-carboxylic acid tert-butyl ester With iron; acetic acid In water at 20℃; for 1.5h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate | 48.2 To a solution of tert-butyl 6- nitroindoline-1-carboxylate (270mg, 1.02mmol) in AcOHTH2O (2.5mL, 10:1, v:v) was added iron powder (229mg, 4.08mmol) portionwise. The resulting mixture was stirred at rt. After 1.5h, the reaction was filtered through Celite and the filtrate concentrated in vacuo. The residue was diluted with EtOAc and the resulting organic layer was washed with sat. NaHCO3 and brine. The organic layer was concentrated in vacuo to yield tert-butyl 6-aminoindoline-l- carboxylate as a grey solid. MS (ES+): m/z 235 [M+l]. 1H NMR (CDCl3, 400MHz): δ 1.55 (s, 9H), 2.96 (t, J= 8.4 Hz, 2H), 3.61 (br.s, 2H), 3.93 (t, J= 8.4 Hz, 2H), 6.27 (d, J= 8.4 Hz, IH), 6.89 (d, J= 8.4 Hz, IH), 7.30 (s, IH). | |
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 25℃; for 16h; | To a mixture of <strong>[19727-83-4]6-nitroindoline</strong> (2 mmol) and TEA (2.2 mmol) in CH2Cl2 (20 mL) was added di-tert-butyl dicarbonate (2 mmol). The mixture was stirred at 25 C. for 16 h. The mixture was washed with satd. aq. NaHCO3 (20 mL) and brine (20 mL), and then was dried and concentrated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With pyridine; dmap; In dichloromethane; | To a stirred solution of <strong>[19727-83-4]6-nitroindoline</strong> (8.0 g, 48.8 mmol) in DCM (50 ml_) was added pyridine (9.9 ml_, 122 mmol), (Boc)2O (10.6g, 48.6 mmol) and catalytic DMAP. EPO <DP n="35"/>The mixture was stirred overnight. Reaction was washed with brine, and the organic layer was dried (Na2SO4), filtered and concentrated. Chromatography (20% EtOAc/hexanes) provided 1-Boc-<strong>[19727-83-4]6-nitroindoline</strong> (10 g, 78%). |
50% | With triethylamine; In dichloromethane; at 20℃; for 5h; | To a solution of <strong>[19727-83-4]6-nitroindoline</strong> (a) (3 g, 18.3 mmol) in DCM (30mL) was added di-tert-butyl dicarbonate (4.8 g, 22 mmol) and TEA (3.7 g, 36.6 mmol). The solution was stirred for 5 h at room temperature then washed with water and brine. The organic layer was dried, filtered and concentrated. Silica gel column chromatography provided tert-butyl <strong>[19727-83-4]6-nitroindoline</strong>-l-carboxylate (b) as a white solid (2.4 g, 50%). |
With dmap; In dichloromethane; at 17 - 25℃; for 16h; | 7-(2-methoxyethoxy)quinazolin-4-yloxy]phenyl}acetamide used as a starting material was prepared as follows :-Di-tert-butyl dicarbonate (7.2 g) was added to a mixture of <strong>[19727-83-4]6-nitroindoline</strong> (4.92 g) and methylene chloride (50 ml) and the mixture was stirred at ambient temperature for 1 hour. 4-Dimethylaminopyridine (0.37 g) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-mtroindoline- 1-carboxylate as a solid (5.45 g); 1H NMR: (CDCl3) 1.6 (s, 9H), 3.2 (t, 2H), 4.1 (t, 2H), 7.2 (d, IH), 7.85 (d, IH), 8.3 (br s, 0.5H), 8.7 (br s, 0.5H). |
With dmap; In dichloromethane; at 17 - 25℃; for 17h; | The tert-butyl 6-aminoindoline-l-carboxylate used as a starting material was prepared as follows :-Di-tert-butyl dicarbonate (7.2 g) was added to a mixture of <strong>[19727-83-4]6-nitroindoline</strong> (4.92 g) and methylene chloride (50 ml) and the mixture was stirred at ambient temperature for 1 hour. 4-Dimethylaminopyridine (0.37 g) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60C) and ethyl acetate as eluent. There was thus obtained tert-butyl <strong>[19727-83-4]6-nitroindoline</strong>- 1-carboxylate as a solid (5.45 g); 1H NMR: (CDCl3) 1.6 (s, 9H), 3.2 (t, 2H), 4.1 (t, 2H), 7.2 (d, IH), 7.85 (d, IH), 8.3 (br s, 0.5H), 8.7 (br s, 0.5H). | |
With dmap; In tetrahydrofuran; at 20℃; | To a solution of nitroindoline(0.54g, 3.29mmol) in THF (7mL) was added di-tert-butyl dicarbonate (0.72g, 3.29mmol) and DMAP (0.44g, 3.62mmol) . The resulting mixture was stirred overnight at rt. The reaction was then diluted with EtOAc and washed with IN HCl. The organic layer was neutralized with sat. NaHCO3, washed with sat. NaCl (2x), dried over Na2SO4, filtered, and concentrated in vacuo to yield tert-butyl <strong>[19727-83-4]6-nitroindoline</strong>-l-carboxylate as a yellow solid. MS (ES+): m/z EPO <DP n="46"/>265 [M+l]. 1H NMR (d6-DMSO, 400MHz): delta 1.49 (s, 9H), 3.16 (t, J= 8.8 Hz, 2H), 3.98 (t, J= 8.8 Hz, 2H), 7.42 (d, J= 8.4 Hz, IH), 7.81 (dd, J= 8.4 Hz, 2.0 Hz, IH), 8.41 (s, IH). |