Structure of Benzylisatin
CAS No.: 1217-89-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1217-89-6 |
Formula : | C15H11NO2 |
M.W : | 237.25 |
SMILES Code : | O=C1N(CC2=CC=CC=C2)C3=C(C=CC=C3)C1=O |
MDL No. : | MFCD00187663 |
InChI Key : | SIISFRLGYDVIRG-UHFFFAOYSA-N |
Pubchem ID : | 264734 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
* 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 |
---|---|---|
77% | With triethylamine; In ethanol; at 40℃; for 2h; | The 1-benzyl-isatin (2.37g, 10mmol) and 6-chloro -2,3-dihydro-quinolin-4-one (1.81g, 10mmol) is dissolved in Anhydrous ethanol (10 ml) in, then adding triethylamine (0.5 ml), heating the system to 40 C, stirring reaction 2h, the separated solid filtering, anhydrous ethanol (2×1 ml) washing, vacuum drying, to get the yellow solid 3.21g, yield 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium tert-butylate; In toluene; at 20℃;Inert atmosphere; | General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 × 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; at 30℃; for 12h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30°C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol; at 30℃; for 28h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |