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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. : | 7149-14-6 | 
| Formula : | C6H3BrINO2 | 
| M.W : | 327.90 | 
| SMILES Code : | O=[N+](C1=CC=C(I)C(Br)=C1)[O-] | 
| MDL No. : | MFCD09878135 | 
| InChI Key : | CJUZKENURNQSDJ-UHFFFAOYSA-N | 
| Pubchem ID : | 238706 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H302-H315-H319-H335 | 
| Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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.

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 77% | With potassium iodide; sodium nitrite; In water; acetonitrile; at 0 - 5℃; for 0.5h; | Ice-cold solution of sodium nitrite (57.2 g, 829 mmol) and potassium iodide (138 g, 829 mmol) in water (25 mL) was added drop wise simultaneously to a stirred suspension of 2-bromo-4-nitroaniline (60 g, 276 mmol) in acetonitrile (250 mL) at 0-5 C and stirred for 30 minutes. The reaction mixture was then poured on to ice-cold water (1000 mL). The solid obtained was filtered, washed with water and dried to afford the titlecompound.Yield: 70.0 g (77 %); 1H NMR (300 MHz, CDCI3): O 7.86 (dd, 1H, J= 8.7, 2.4 Hz, Ar), 8.10(d, 1H, J= 8.7 Hz, Ar), 8.45 (d, 1H, J= 2.4 Hz, Ar); MS (El, 70 eV): m/z 328.3 (M+H). | 
 [ 7149-14-6 ]
                                                    
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                                                    [ 7149-14-6 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 89% | With potassium carbonate; triethylamine; In 1-methyl-pyrrolidin-2-one; at 90℃; for 2h; | Palladium acetate (0.147 g, 0.656 mmol) and triethylamine (7.31 mL, 52.5 mmol) were added to a stirred solution of the compound of example 124 (4.3 g, 13.11 mmol) and ethyl acrylate (6.98 mL, 65.6 mmcl) in NMP (20 mL) and heated to 90 C for 2 h. The reaction mixture was cooled, diluted with 1M HCI (200 mL) and extracted with ethyl acetate (2x50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and evaporated the solvent to afford the title compound.Yield: 3.6 g (89.0 %); 1H NMR (300 MHz, CDCI3): O 1.38 (t, 3H, J= 6.9 Hz, CH3), 4.33 (q, 2H, J= 6.9 Hz, CH2), 6.55 (d, 1H, J= 15.5 Hz, CH), 7.73 (d, 1H, J= 7.5 Hz, Ar), 8.03 (d, 1H, J= 15.9 Hz, CH), 8.21(d, 1H, J= 8.4 Hz, Ar), 8.51(d, 1H, J = 1.8 Hz, Ar); MS (El, 70 eV): mlz 300.1 (M+H). | 

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