Structure of 1782897-37-3
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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. : | 1782897-37-3 |
| Formula : | C11H12BrNO2 |
| M.W : | 270.12 |
| SMILES Code : | O=C(C1=CC2=C(NCCC2)C(Br)=C1)OC |
| English Name : | Methyl 8-bromo-1,2,3,4-tetrahydroquinoline-6-carboxylate |
| MDL No. : | MFCD28650951 |
* 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 |
|---|---|---|
| Multi-step reaction with 6 steps 1: lithium hydroxide / tetrahydrofuran; water; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); Xantphos / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere 6: hydrogen; Pd/C / ethyl acetate / 6 h / 20 °C | ||
| Multi-step reaction with 6 steps 1.1: water; lithium hydroxide / tetrahydrofuran; methanol / 4 h / 50 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4.1: tetrahydrofuran / 6 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 5.2: 12 h / 100 °C / Inert atmosphere 6.1: hydrogen; 10% Pd/C / ethyl acetate / 6 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 87% | With water monomer; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 50℃; for 4h; | 30.2 Step 2: Synthesis of 8-bromo-l,2,3,4-tetrahydroquinoline-6-carboxylic acid To a solution of methyl l°2°3°4-tetrahydroquinoline-8-bromo-6-carboxylate (2.9 g° 10.1 mmol) in THF° MeOH and H2O (3:1:1; 30 mL)° was added LiOH (851 mg° 20.3 mmol) and the reaction mixture was stirred at 50 °C for 4 h. The volatiles were evaporated under reduced pressure and diluted with EtOAc. The pH was adjusted to ~2 with in 1 N aqueous HCI and the aqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers were dried (Na2S04)° filtered and concentrated under reduced pressure to afford title compound as a solid” which was used in the next step without further purification. LC-MS m/z: ES+ [M+H]+ = 256.0; tR = 2.20 min. |
| 87% | With water monomer; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 50℃; for 4h; | 30.2 Step 2: Synthesis of 8-bromo-l,2,3,4-tetrahydroquinoline-6-carboxylic acid To a solution of methyl l°2°3°4-tetrahydroquinoline-8-bromo-6-carboxylate (2.9 g° 10.1 mmol) in THF° MeOH and H2O (3:1:1; 30 mL)° was added LiOH (851 mg° 20.3 mmol) and the reaction mixture was stirred at 50 °C for 4 h. The volatiles were evaporated under reduced pressure and diluted with EtOAc. The pH was adjusted to ~2 with in 1 N aqueous HCI and the aqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers were dried (Na2S04)° filtered and concentrated under reduced pressure to afford title compound as a solid” which was used in the next step without further purification. LC-MS m/z: ES+ [M+H]+ = 256.0; tR = 2.20 min. |
| With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water monomer at 50℃; for 4h; | 30.2 [0336] Step 2: Synthesis of 8-bromo-l,2,3 tetrahydroquinoline-6-carboxylic acid To a solution of methyl l,2,3,4-tetrahydroquinoline-8-bromo-6-carboxylate (2.9 g, 10.1 mmol) in THF, MeOH and H20 (3:1:1; 30 mL), was added LiOH (851 mg, 20.3 mmol) and the reaction mixture was stirred at 50 °C for 4 h. The volatiles were evaporated under reduced pressure and diluted with EtOAc. The pH was adjusted to ~2 with in 1 N aqueous HCI and the aqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure to afford title compound as a solid, which was used in the next step without further purification. LC-MS m/z: ES+ [M+H]+ = 256.0; tR = 2.20 min. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C | ||
| Multi-step reaction with 2 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C | ||
| Multi-step reaction with 3 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C | ||
| Multi-step reaction with 4 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: Cs2CO3; copper (I) iodide; ammonium hydroxide; acetylacetone / N,N-dimethyl-formamide / 6 h / 110 °C | ||
| Multi-step reaction with 5 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: Cs2CO3; copper (I) iodide; acetylacetone; ammonium hydroxide / N,N-dimethyl-formamide / 110 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 6 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: Cs2CO3; copper (I) iodide; ammonium hydroxide; acetylacetone / N,N-dimethyl-formamide / 6 h / 110 °C 6: triethylamine; dmap / dichloromethane / 12 h / 20 °C | ||
| Multi-step reaction with 6 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: Cs2CO3 / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: Cs2CO3; copper (I) iodide; acetylacetone; ammonium hydroxide / N,N-dimethyl-formamide / 110 °C 6: triethylamine; dmap / dichloromethane / 0 - 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 7 steps 1: lithium hydroxide / tetrahydrofuran; water; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: caesium carbonate; copper(l) iodide; ammonium hydroxide; acetylacetone / N,N-dimethyl-formamide / 6 h / 110 °C 6: triethylamine; dmap / dichloromethane / 12 h / 20 °C 7: hydrogen; 10% Pd/C / ethyl acetate / 6 h / 20 °C | ||
| Multi-step reaction with 7 steps 1: water; lithium hydroxide / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4: tetrahydrofuran / 6 h / 0 - 20 °C 5: caesium carbonate; copper(l) iodide; acetylacetone; ammonium hydroxide / N,N-dimethyl-formamide / 110 °C 6: triethylamine; dmap / dichloromethane / 0 - 20 °C 7: hydrogen; 10% Pd/C / ethyl acetate / 6 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: dmap / tetrahydrofuran / 12 h / 68 °C | ||
| Multi-step reaction with 3 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: dmap / tetrahydrofuran / 12 h / 68 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water monomer; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3: dmap / tetrahydrofuran / 12 h / 68 °C 4: tetrahydrofuran / 2 h / 0 - 20 °C | ||
| Multi-step reaction with 4 steps 1: water monomer; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: dmap / tetrahydrofuran / 12 h / 68 °C 4: tetrahydrofuran / 2 h / 0 - 20 °C |