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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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    							Batch number can be found on the product's label following the word 'Batch'.
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| CAS No. : | 36517-91-6 | 
| Formula : | C11H10O4 | 
| M.W : | 206.20 | 
| SMILES Code : | O=C1CC(C2=C1C=C(OC)C(OC)=C2)=O | 
| MDL No. : | MFCD25962764 | 
| InChI Key : | OFQWGNIJXMWOGZ-UHFFFAOYSA-N | 
| Pubchem ID : | 12384295 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H302-H315-H319-H335 | 
| Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | 
* 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.

 [ 36517-91-6 ]
                                                    
                                                    [ 36517-91-6 ]
 [ 58084-22-3 ]
                                                    
                                                    [ 58084-22-3 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 64% | With caesium carbonate; copper(l) chloride; In acetonitrile; at 90℃; for 3.5h; | 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.219 g, 1.5 mmol), cesium carbonate (0.39 g, 1.2 mmol) in a 50 mL round bottom flask.Add 10-15 mL of acetonitrile and heat it in an oil bath preheated to 90 C for 5 minutes.Copper chloride (6.7 mg, 5 mol%) was added and a reflux tube was placed, and the reaction was terminated by a TLC sheet. After the reaction was completed, the mixture was returned to room temperature, and 1-2 mL of saturated brine was added thereto, followed by concentration and concentration to remove acetonitrile. After adding iced saturated brine to solidify the product, gravity has passedFiltration and washing with water gave the pure product compound (1). Weighing 199 mg, the yield was 76%. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 69% | With caesium carbonate; copper(l) chloride; In acetonitrile; at 90℃; for 4.5h; | 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.219 g, 1.5 mmol), cesium carbonate (0.39 g, 1.2 mmol) in a 50 mL round bottom flask.Add 10-15 mL of acetonitrile and heat it in an oil bath preheated to 90 C for 5 minutes.Copper chloride (6.7 mg, 5 mol%) was added and a reflux tube was placed, and the reaction was terminated by a TLC sheet. After the reaction was completed, the mixture was returned to room temperature, and 1-2 mL of saturated brine was added thereto, followed by concentration and concentration to remove acetonitrile. After adding iced saturated brine to solidify the product, gravity has passedFiltration and washing with water gave the pure product compound (1). Weighing 199 mg, the yield was 76%. | 
 [ 36517-91-6 ]
                                                    
                                                    [ 36517-91-6 ]

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 73% | With caesium carbonate; copper(l) chloride; In acetonitrile; at 90℃; for 1h; | 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.219 g, 1.5 mmol), cesium carbonate (0.39 g, 1.2 mmol) in a 50 mL round bottom flask.Add 10-15 mL of acetonitrile and heat it in an oil bath preheated to 90 C for 5 minutes.Copper chloride (6.7 mg, 5 mol%) was added and a reflux tube was placed, and the reaction was terminated by a TLC sheet. After the reaction was completed, the mixture was returned to room temperature, and 1-2 mL of saturated brine was added thereto, followed by concentration and concentration to remove acetonitrile. After adding iced saturated brine to solidify the product, gravity has passedFiltration and washing with water gave the pure product compound (1). Weighing 199 mg, the yield was 76%. | 
 [ 36517-91-6 ]
                                                    
                                                    [ 36517-91-6 ]

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 72% | With copper(ll) sulfate pentahydrate; caesium carbonate; In water; at 130℃; for 0.75h;Sealed tube; | General procedure: 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.161 g, 1.1 mmol), cesium carbonate (0.39 g, 1.2 mmol) and copper sulfate pentahydrate (1.25 mg, 5 μmol) in a 100 mL high pressure tube, add 5 mL of water, and then seal the tube.The mixture was rapidly stirred in an oil bath previously heated to 130 C, and it was checked by a TLC sheet whether or not the reaction was completed. After the reaction was completed, the mixture was returned to room temperature, centrifuged, washed with water, and the tube was dried in an oven to obtain a pure product compound (1). Weighing 214 mg, the yield was 82%. | 
 [ 36517-91-6 ]
                                                    
                                                    [ 36517-91-6 ]

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 61% | With caesium carbonate; copper(l) chloride; In acetonitrile; at 90℃; for 4h; | 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.219 g, 1.5 mmol), cesium carbonate (0.39 g, 1.2 mmol) in a 50 mL round bottom flask.Add 10-15 mL of acetonitrile and heat it in an oil bath preheated to 90 C for 5 minutes.Copper chloride (6.7 mg, 5 mol%) was added and a reflux tube was placed, and the reaction was terminated by a TLC sheet. After the reaction was completed, the mixture was returned to room temperature, and 1-2 mL of saturated brine was added thereto, followed by concentration and concentration to remove acetonitrile. After adding iced saturated brine to solidify the product, gravity has passedFiltration and washing with water gave the pure product compound (1). Weighing 199 mg, the yield was 76%. | 
 [ 36517-91-6 ]
                                                    
                                                    [ 36517-91-6 ]

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 65% | With caesium carbonate; copper(l) chloride; In acetonitrile; at 90℃; for 16h; | 2-iodobenzamide 1a (0.261 g, 1 mmol), 1,3-indanedione 2a (0.219 g, 1.5 mmol), cesium carbonate (0.39 g, 1.2 mmol) in a 50 mL round bottom flask.Add 10-15 mL of acetonitrile and heat it in an oil bath preheated to 90 C for 5 minutes.Copper chloride (6.7 mg, 5 mol%) was added and a reflux tube was placed, and the reaction was terminated by a TLC sheet. After the reaction was completed, the mixture was returned to room temperature, and 1-2 mL of saturated brine was added thereto, followed by concentration and concentration to remove acetonitrile. After adding iced saturated brine to solidify the product, gravity has passedFiltration and washing with water gave the pure product compound (1). Weighing 199 mg, the yield was 76%. | 

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