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CAS No. : | 114417-34-4 | MDL No. : | MFCD12028725 |
Formula : | C9H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MZRDGUADMZHLRW-UHFFFAOYSA-N |
M.W : | 226.07 | Pubchem ID : | 14501409 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
52% | With hydrogenchloride In isopropyl alcohol for 17h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With hydrogenchloride; acetic acid for 3.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / Heating 2: 1) NH2OSO3H, 2) aq. K2CO3 / 1) MeOH, CH2Cl2, r.t., 2) MeOH, CH2Cl2, r.t. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 0.33 h / Heating 2: aq. HCl / dioxane / 3 h / Heating 3: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 4: 30 percent / gl. AcOH, aq. HCl / 3.5 h / Heating | ||
Multi-step reaction with 4 steps 1: pyridine / 2 h / 20 °C 2: water; hydrogenchloride / 1,4-dioxane / 5 h / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 4: aluminum (III) chloride / dichloromethane / 3 h / 5 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 52 percent / conc. HCl / propan-2-ol / 17 h / Heating 2: 65 percent / benzyltriethylammonium chloride, 50percent NaOH / toluene / 5 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 52 percent / conc. HCl / propan-2-ol / 17 h / Heating 2: 65 percent / benzyltriethylammonium chloride, 50percent NaOH / toluene / 5 h / 70 °C 3: 92 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 0.67 h / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 2: 30 percent / gl. AcOH, aq. HCl / 3.5 h / Heating | ||
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 2: aluminum (III) chloride / dichloromethane / 3 h / 5 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aq. HCl / dioxane / 3 h / Heating 2: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 3: 30 percent / gl. AcOH, aq. HCl / 3.5 h / Heating | ||
Multi-step reaction with 3 steps 1: water; hydrogenchloride / 1,4-dioxane / 5 h / Reflux 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 3: aluminum (III) chloride / dichloromethane / 3 h / 5 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: AcOH / 22 h / Heating 2: pyridine / 0.33 h / Heating 3: aq. HCl / dioxane / 3 h / Heating 4: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 5: 30 percent / gl. AcOH, aq. HCl / 3.5 h / Heating | ||
Multi-step reaction with 5 steps 1: acetic acid / 16 h / Reflux 2: pyridine / 2 h / 20 °C 3: water; hydrogenchloride / 1,4-dioxane / 5 h / Reflux 4: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 5: aluminum (III) chloride / dichloromethane / 3 h / 5 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: formaldehyd; 7-bromo-2,3-dihydroquinolin-4(1H)-one With acetic acid In 1,2-dichloro-ethane at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 18h; | 102D Example 102D; A mixture of 0.25 g ( 1.1 mMol) of the product from example 102C, 0.23 g (7.7 mMol) of paraformaldehyde and a drop of glacial acetic acid in 1 mls of dichloroethane was stirred for 30 minutes at ambient temperature. 1.1 g (5.5 mMol) of sodium triacetoxyborohydride was added and the reaction stirred for 18 hours at ambient temperature. 100 mls of ethyl acetate was added and then washed with 10% NaHCO3, 5% citric acid, saturated NaCl, the organic layer dried with MgSO4, filtered, and the solvent evaporated. The residue was purified by flash chromatography using a gradient from hexane to 50% ethyl acetate in hexane to provide Example 102D. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-(3-bromo-phenyl)-azetidin-2-one With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Stage #2: With sodium hydrogencarbonate In water; 1,2-dichloro-ethane | 102C Example 102C; 5.0 g (33 mMol) of trifluoromethanesulfonic acid [CAS No. 1493-13-6] was added to a solution of 28 mMol of the compound from example 102B in 250 mls of dichloroethane and the solution was stirred for 1 hour at ambient temperature. The reaction was washed with 10% NaHCO3, water, and saturated NaCl the organic layer was dried with MgSO4, filtered and the solvent evaporated. The resulting oil was further purified by flash chromatography using a gradient from hexane to 40% ethyl acetate in hexane then 100% ethyl acetate to provide Example 102C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With aluminum (III) chloride In dichloromethane at 5 - 20℃; for 3h; | 98 Preparation of 7-bromo-2,3-dihydroquinolin-4(1H)-one [03511 A solution of 3 -(N-(3 -bromophenyl)-4-methylphenylsulfonamido)propanoic acid (5.00 g, 12.59 mmol), SOd2 (4.60 mL , 62.97 mmol) and one drop of DMF in DCM (20 mL) was refluxed for 2 h. Then the solution was concentrated to dryness to give carboxylic chloride which was used for next step. A mixture of A1C13 (3.40 g, 25.18 mmol) in DCM (20 mL) was cooled at 5 °C, and then a solution of carboxylic chloride prepared above in DCM (10 mL) was added dropwise over 30 mm. After addition, the solution was stirred at room temperature for 3 h. Then the solution was quenched with ice water, neutralized with NaOH solution, and extracted with EtOAc (50 mL x 3). The combined organic phase was dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 1/4) to give product 7-bromo-2,3-dihydroquinolin-4(1H)-one as a yellow solid (1.86 g, yield: 54%). ESI-MS (M+H): 226.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 70 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 70 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 80 °C 3: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dimethoxyethane / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With pyridine at 70℃; | 188.I Synthesis of 7-Bromo-1-((3-(trifluoromethyl)phenyl)sulfonyl)-2,3- dihydroquinolin-4(1H)-one To 7-bromo-2,3-dihydroqu no n- )-one (0.25 g, 1.1 mmol) in pyridine (5 mL) was added 3-(trifluoromethyl)benzenesulfonyl chloride (0.18 mL, 1.1 mmol) and heated overnight at 70 °C. The reaction mixture was cooled, diluted with ethyl acetate, washed with 1 M aqueous hydrogen chloride three times, and followed by washing with brine. The organic layer was dried (Na2SO4) and concentrated. The resulting residue was purified by MPLC eluting with a gradient of 0-50% ethyl acetate in hexanes. Pure fractions were combined and concentrated to afford 7-bromo-1-((3-(trifluoromethyl)phenyl)sulfonyl)-2,3-dihydroquinolin- 4(1H)-one (230 mg, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride In ethanol at 20℃; for 2h; Cooling with ice; | |
With hydrogenchloride In ethanol at 20℃; for 2h; Cooling with ice; | A Step A: Step A: tert-butyl 7-bromo-4-((4-fluorophenyl)sulfonyl)quinoline-1(2H)-carboxylate A solution of 7-bromo-2,3-dihydroquinolin-4(1H)-one (8.0 g, 35 mmol) and 4-fluorobenzenethiol (7.9 mL, 74 mmol) in ethanol (44 mL) was cooled on an ice-water bath. HCl gas was bubbled through the mixture until saturation was reached (as indicated by the formation of a white precipitate). The mixture was stirred on the ice-water bath for 1 h and at rt for 1 h more. The mixture was concentrated and the resulting oil was dissolved in DCM (250 mL), washed with 1 M aqueous NaOH, dried and concentrated to give crude 7-bromo-4,4-bis((4-fluorophenyl)thio)-1,2,3,4-tetrahydroquinoline as a solid (16.4 g, quantitative yield). HPLC tR 1.27 min (method B). | |
With hydrogenchloride In ethanol at 20℃; for 2h; Cooling with ice; | A Step A: tert-butyl 7-bromo-4-((4-fluorophenyl)sulfonyl)iuinoline- 1 (2H)-carboxylate A solution of 7-bromo-2,3-dihydroquinolin-4(1B)-one (8 g, 35 minol), 4- fluorobenzenethiol (7.9 mL, 74 minol) and absolute ethanol (44 mL) was cooled with an ice-water bath. HC1 gas was bubbled through the mixture until saturation was reached (as indicated by the formation of a white precipitate). The mixture was stirred on the ice- water bath for 1 h and at rt for 1 h more. The mixture was concentrated and the resultingoil was dissolved in DCM (250 mL) and washed with 1 M aqueous NaOH. The organic phase was dried and concentrated to give crude 7-bromo-4,4-bis((4-fluorophenyl)thio)- 1,2,3,4-tetrahydroquinoline as a solid (16.4 g, 100% yield). HPLC tR 1.27 min (methodA). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C | ||
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice | ||
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice | ||
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: activated copper / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube; Inert atmosphere 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice | ||
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: activated copper / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: activated copper / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube; Inert atmosphere 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 10: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18.5 h / 20 °C 11: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: activated copper / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube; Inert atmosphere 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 10: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: activated copper / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube; Inert atmosphere 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 10: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18.5 h / 20 °C 11: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 12: acetic acid; sodium tetrahydroborate / water; methanol / 96 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / Cooling with ice 4: tetrahydrofuran / 0.5 h / 5 °C / Cooling with ice 5: triethylamine / dichloromethane / 0.5 h / 20 °C | ||
Multi-step reaction with 5 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C 11: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C 11: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C 12: sodium cyanoborohydride / water; methanol; acetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C 11: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C 12: sodium cyanoborohydride / water; methanol; acetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C 11: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C 12: sodium cyanoborohydride / water; methanol; acetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran / 2 h / 20 °C 11: sodium cyanoborohydride / water; methanol; acetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 4: tetrahydrofuran / 0.5 h / 0 °C 5: triethylamine / dichloromethane / 0.5 h / 20 °C 6: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 8: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere; Sealed tube 9: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol / 2 h / 20 °C / Cooling with ice 2: dmap / 1,4-dioxane / 16 h / 20 °C |
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