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CAS No. : | 113023-73-7 | MDL No. : | MFCD00020378 |
Formula : | C9H9BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VICCYULHZWEWMB-UHFFFAOYSA-N |
M.W : | 229.07 | Pubchem ID : | 5146225 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
92% | With acetyl chloride at 0 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,3-di(thiophen-2-yl)propenone; Cyanothioacetamide With sodium methylate In methanol Stage #2: 4-(1-bromoethyl)-benzoic acid With caesium carbonate In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating 3: 71 percent / fuming nitric acid / 1 h / -10 °C 4: 80 percent / aq. hydrazine / ethanol / 2.25 h / 50 °C 5: 91 percent / DIEA / dimethylformamide 6: 87 percent / K2CO3 / H2O; methanol / 20 h 7: 7 percent / NADase / H2O / 8 h / 37 °C / pH 7.3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating 3: 71 percent / fuming nitric acid / 1 h / -10 °C 4: 80 percent / aq. hydrazine / ethanol / 2.25 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating 3: 71 percent / fuming nitric acid / 1 h / -10 °C 4: 80 percent / aq. hydrazine / ethanol / 2.25 h / 50 °C 5: 91 percent / DIEA / dimethylformamide 6: 87 percent / K2CO3 / H2O; methanol / 20 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating 3: 71 percent / fuming nitric acid / 1 h / -10 °C 4: 80 percent / aq. hydrazine / ethanol / 2.25 h / 50 °C 5: 91 percent / DIEA / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 92 percent / AcCl / 0 - 25 °C 2: 85 percent / dimethylformamide / 1 h / Heating 3: 71 percent / fuming nitric acid / 1 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In diethyl ether; ethyl acetate; N,N-dimethyl-formamide | 3 4-[3-(2-{1-[4-carboxyphenyl]-ethylamino}-phenyl)-ureido]-benzonitrile Example 3 4-[3-(2-{1-[4-carboxyphenyl]-ethylamino}-phenyl)-ureido]-benzonitrile 12.8 g (88.8 mmol) 4-cyanophenylisocyanat were dissolved in 500 ml diethyl ether at rt. 9.6 g (88.8 mmol) o-phenylene diamine were added with stirring. After stirring overnight, the reaction mixture was filtrated and the solid washed with diethylether. The so prepared mono-urea derivative was sufficient pure for further reactions. 3.78 (15 mmol) were dissolved in 30 ml anhydrous dry DMF, 3.44 g (15 mmol) 4-(1-bromoethyl)-benzoic acid and 2 g potassium carbonate were added and stirred for 3 days at rt. The solvent was removed under reduced pressure, the product dissolved in ethyl acetate and extracted with 1 m HCl, water and brine. The organic phase was dried over sodium sulfate and the solvent removed under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In methanol; ethyl acetate | 64.A Step A. Step A. Preparation of methyl R,S-4-(1-bromoethyl)-benzoate 2.5 g (10 mmol) of 4-(1-bromoethyl)-benzoic acid was dissolved in 100 ml of methanol and treated with 1 ml of concentrated sulfuric acid. The solution was stirred for 18 hours, concentrated in vacuo and the residue was dissolved in 100 ml of EtOAc. The solution was washed with saturated sodium bicarbonate solution (3*25 ml) and was dried over MgSO4, filtered and was concentrated in vacuo to give 1.5 g of an oil. 300 MHz 1H NMR (CDCl3): 2.05 (d, 3H); 3.91 (s, 3H); 5.20 (q, 1H); 7.50 (d, 2H); 8.00 (d, 2H). | |
With sodium hydroxide; benzotriazol-1-ol In methanol; chloroform | 9.1 Example 9-1 Example 9-1 Synthesis of methyl 4-bromoethylbenzoate (Compound IV-2) Commercially available 4-bromoethylbenzoic acid (997.9 mg) was dissolved in methanol (30 ml). After the addition of WSCI hydrochloride (1.2527 g) and HOBt (598.5 mg), the solution was stirred for 24 hours at 60°C. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, washed with 1 mol/l hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography to obtain the title compound (829.5 mg) as a colorless solid. MS(FAB,Pos.):m/z=243,245[M+1]+ 1H-NMR(60MHz,CDCl3):δ=3.0-3.5(2H,m),3.5-3.9(2H,m),3.91(3H, s),7.1-7.4(2H,m),7.8-8.1(2H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium azide In water; acetone at 20℃; | |
With sodium azide In N,N-dimethyl-formamide at 40℃; | 31 The tetrapeptide was coupled to the N-terminal capping group. The capping groups was prepared by reacting 1-bromo-1-(4-benzoic acid) ethane with sodium azide, reducing the resulting azide to the amine and coupling the product with the tetrapeptide. Step K: Formation of AzideThe Halide (5.5 mmole) was dissolved in dry DMF and sodium azide (6.88 mmole) was added. The reaction was stirred overnight under nitrogen at 40° C. Workup: the reaction was concentrated under vacuum and partitioned between ethyl acetate and water. The organic layer was dried by MgSO4. The azide product was obtained in 89% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With thionyl chloride at 0 - 70℃; for 2h; Inert atmosphere; | |
With sulfuric acid at 20℃; | 10 Intermediate 10: Methyl 4-(1-bromoethyl)benzoateDissolve 4-(1-bromoethyl)benzoic acid (2.18×10-3 mol) in methanol (12 ml). Place the mixture under stirring and then slowly add sulphuric acid (0.5 ml). After stirring for one night at ambient temperature, the reaction mixture is poured into water (50 ml). Extract with dichloromethane (3×30 ml). The organic phase is washed with brine, dried over magnesium sulphate, filtered and then evaporated to dryness under reduced pressure.The title product is obtained in the form of a colourless oil which is used without subsequent purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol In diethyl ether at 0℃; for 1h; | 14.4.1 Intermediate 14.4.1 4-(1 -Bromo-ethyl)-benzoic acid methyl esterA solution of 4-(1 -bromo-ethyl)-benzoic acid (2.70 g, 1 1 .8 mmol) in diethyl ether (20 mL) and methanol (5 mL) was cooled to 0°C and treated with trimethylsilyldiazomethane (2 M in diethylether, 1 1 .8 mL). After 1 h at 0° C the solvents were removed under reduced pressure, the residue was re-dissolved in ethyl acetate (20 mL) and washed with aqueous NaHC03 solution. The organic layer was collected, dried over MgS04 and evaporated under reduced pressure.Yield: 3.0 gESI mass spectrum: [M+H]+ = 243/245 (Br)Retention time HPLC: 2.80 min (method F) | |
With methanol In diethyl ether at 0℃; for 1h; | 14.4.14.4.1 Example 14.4(1-{4-[1-(3,4-Dichloro-phenoxy)-ethyl]-benzyl}-3,5-dimethyl-1H-pyrazol-4-yl)-acetic acidIntermediate 14.4.14-(1-Bromo-ethyl)-benzoic acid methyl esterA solution of 4-(1-bromo-ethyl)-benzoic acid (2.70 g, 11.8 mmol) in diethyl ether (20 mL) and methanol (5 mL) was cooled to 0° C. and treated with trimethylsilyldiazomethane (2 M in diethylether, 11.8 mL). After 1 h at 0° C. the solvents were removed under reduced pressure, the residue was re-dissolved in ethyl acetate (20 mL) and washed with aqueous NaHCO3 solution. The organic layer was collected, dried over MgSO4 and evaporated under reduced pressure.Yield: 3.0 gESI mass spectrum: [M+H]+=243/245 (Br)Retention time HPLC: 2.80 min (method F) | |
In tetrahydrofuran; methanol at 0 - 23℃; for 3h; | 6.A Step A. Methyl 4-(l-bromoethyl benzoate INTERMEDIATES 6A & 6B Intermediate 6A Intermediate 6B (IR.2S and IS, 2R)-l-Methyl-2'-oxo-l . l'.2'.3-tetrahvdrospirorindene-2.3'-pyrrolor2.3- blpyridinel-5-carboxylic acid (Intermediate 6 A) and (1R.2R and IS, 2S)- 1 -methyl-2'-oxo- U',2',3-tetrahvdrospirorindene-2,3'-pyrrolor2,3-b1pyridine1-5-carboxylic acid (Intermediate 6B) Step A. Methyl 4-(l-bromoethyl benzoate A solution of trimethylsillyldiazomethane in THF (2M, 49.1 mL, 98.3 mmol) was added dropwise to a solution of 4-(l-bromoethyl)benzoic acid (15 g, 66 mmol) in methanol (75 mL) and THF (75 mL) at 0 °C. The resulting mixture was stirred at 23 °C for 3 h, then concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (2x). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound. XH NMR (400 MHz, CDC13): δ 8.02 (d, 2H, J= 8.5 Hz), 7.51 (d, 2H, J= 8.2 Hz), 5.21 (q, 1H, J= 6.7 Hz), 3.92 (s, 3H), 2.06 (d, 3H, J= 7.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / diethyl ether / 1 h / 0 °C 2: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol; tetrahydrofuran / 3 h / 0 - 23 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 23 °C 2.2: 5.25 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol; tetrahydrofuran / 3 h / 0 - 23 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 23 °C 2.2: 5.25 h / 0 - 20 °C 3.1: potassium carbonate / tetrahydrofuran / 20 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol; tetrahydrofuran / 3 h / 0 - 23 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 23 °C 2.2: 5.25 h / 0 - 20 °C 3.1: potassium carbonate / tetrahydrofuran / 20 h / Reflux 4.1: trifluoroacetic acid / dichloromethane / 5 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanol; tetrahydrofuran / 3 h / 0 - 23 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 23 °C 2.2: 5.25 h / 0 - 20 °C 3.1: potassium carbonate / tetrahydrofuran / 20 h / Reflux 4.1: trifluoroacetic acid / dichloromethane / 5 h / 23 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanol; tetrahydrofuran / 3 h / 0 - 23 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 23 °C 2.2: 5.25 h / 0 - 20 °C 3.1: potassium carbonate / tetrahydrofuran / 20 h / Reflux 4.1: trifluoroacetic acid / dichloromethane / 5 h / 23 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 23 °C 6.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / N,N-dimethyl-formamide / 0.33 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
441 mg | With sodium hydroxide In water at 20℃; for 16h; | 1 Example 1 Intermediate 1 4-(1-[5-(3,4-Dimethylphenyl)-1,3,4-oxadiazol-2-yl]thio}ethyl)benzoic acid Example 1 Intermediate 1 RRN 3 4-(1-[5-(3,4-Dimethylphenyl)-1,3,4-oxadiazol-2-yl]thio}ethyl)benzoic acid [0080] 5-(3,4-dimethylphenyl)-1,3,4-oxadiazole-2-thiol CAS[108413-56-5](570 mg, 2.76 mmol) and 4-(1-bromoethyl)-benzoic acid CAS [113023-73-7](634 mg, 2.76 mmol) in water (13 mL) was added NaOH (1M, 6 mL). After stirring at RT for 16 h, the reaction mixture pH was adjusted to 2 upon addition of aqueous solution of HCl (10%). The precipitate was collected by filtration. The solid was dissolved in acetone and purified by MPLC (30-70% ethyl acetate in hexanes) to afford 441 mg of Intermediate 1 as a colorless solid. [0082] 1H NMR (300 MHz, CD3OD) δ 7.96-8.01 (m, 2H), 7.55-7.60 (m, 4H), 7.23 (d, J=8.50 Hz, 1H), 5.03 (q, J=7.13 Hz, 1H), 2.20-2.36 (m, 6H), 1.83 (d, J=7.03 Hz, 3H). |
441 mg | With sodium hydroxide In water at 20℃; for 16h; | 1 4-(1-{ [5-(3,4-Dimethylphenyl)-1,3,4-oxadiazol-2-yl]thio}ethyl)benzoic acid [0133] To a solution of 5-(3,4-dimethylphenyl)- 1 ,3,4-oxa-diazole-2-thiol CAS[108413-56-5] (570 mg, 2.76 mmol) and4-(1 -bromoethyl)-benzoic acid CAS [113023-73-71(634mg,2.76 mmol) in water (13 mL)was added NaOH (1 M, 6 mL).Afier stirring at RT for 16 h, the reaction mixture pH was adjusted to 2 upon addition of aqueous solution of HC1 (10%). The precipitate was collected by filtration. The solid was dissolved in acetone and purified by MPLC (30-70% ethyl acetate in hexanes) to afford 441 mg of Intermediate 1 as a colorless solid.[0134] 1H NMR (300 MHz, CD3OD) δ 7.96-8.01 (m, 2H),7.55-7.60 (m, 4H), 7.23 (d, J=8.50 Hz, 1 H), 5.03 (q, J=7.13 Hz, 1 H), 2.20-2.36 (m, 6H), 1.83 (d, J=7.03 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 16 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C 3: pyridinium chlorochromate; periodic acid / acetonitrile / 0.75 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water / 16 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.1: pyridinium chlorochromate; periodic acid / acetonitrile / 0.75 h / 0 °C 4.1: methanol / 2.5 h / 20 °C 4.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; water / 1,2-dimethoxyethane / 90 °C 3.2: 90 °C 4.1: methanol / tetrahydrofuran 5.1: sodium hydroxide / n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With Oxone; water; potassium bromide; In dichloromethane; at 20℃; for 20h;Irradiation; Sealed tube; | General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 × 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With sulfuric acid at 20℃; for 2h; | 2,2-dimethyl-5-nitro-2H-benzimidazole-1,3-dioxide (1) General procedure: To astirred solution of 1 mmol 5-nitrobenzofuroxan (181 mg) in concentratedsulfuric acid (2 mL) 1.7 mmol 2-propanol (102 mg, 0.13 mL) was added dropwiseat room temperature. The reaction mixture was stirred for 2 hours before it waspoured into ice-water and extracted with chloroform (3 x 20 mL). The organiclayer was dried over MgSO4 and evaporated. The crude mixture waspurified by column chromatography on a silica gel (1% MeOH in CHCl3),obtained 165 mg of dark violet solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 3.A Step A: To a mixture of the 4-(1-bromoethyl)benzoic acid (2.29 g, 10.0 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.01 g, 10.5 mmol) in CH2Cl2 (30 mL) at room temperature were added methyl 3-aminopropanoate hydrochloride (1.40 g, 10.0 mmol) and diisopropylethylamine (1.95 mL, 11.0 mmol). The solution was stirred at room temperature for 16 h. The resulting mixture was diluted with CH2Cl2 and washed successively with 1 N aqueous HCl, H2O (twice), brine and then dried over Na2SO4. Filtration and concentration of the filtrate resulted in a residue which was purified by chromatography on silica gel (20% to 50% EtOAc in heptane) to yield a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.75 (d, J=8.3 Hz, 0.9H), 7.74 (d, J=8.1 Hz, 1.1H) (two rotamers 0.9H+1.1H=2H), 7.49 (d, J=8.1 Hz, 1.1H), 7.48 (d, J=8.3 Hz, 0.9H) (two rotamers 0.9H+1.1H=2H), 6.86 (br s, 1H), 5.20 (q, J=6.9 Hz, 0.55H), 5.20 (q, J=6.9 Hz, 0.45H) (two rotamers 0.55H+0.45H=1H), 3.73 (t, J=5.9 Hz, 2H), 3.71 (s, 3H), 2.66 (t, J=5.9 Hz, 2H), 2.04 (d, J=6.9 Hz, 1.65H), 1.84 (d, J=6.9 Hz, 1.35H) (two rotamers 1.65H+1.35H=3H); MS (ES, m/z) 314, 316 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 3.A STEP A To a mixture of the 4-(1-bromoethyl)benzoic acid (2.29 g, 10.0 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.01 g, 10.5 mmol) in CH2Cl2 (30 mL) at room temperature were added methyl 3-aminopropanoate hydrochloride (1.40 g, 10.0 mmol) and diisopropylethylamine (1.95 mL, 11.0 mmol). The solution was stirred at room temperature for 16 h. The resulting mixture was diluted with CH2Cl2 and washed successively with 1 N aqueous HCl, H2O (twice), brine and then dried over Na2SO4. Filtration and concentration of the filtrate resulted in a residue which was purified by chromatography on silica gel (20% to 50% EtOAc in heptane) to yield a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.75 (d, J=8.3 Hz, 0.9H), 7.74 (d, J=8.1 Hz, 1.1H) (two rotamers 0.9H+1.1H=2H), 7.49 (d, J=8.1 Hz, 1.1H), 7.48 (d, J=8.3 Hz, 0.9H) (two rotamers 0.9H+1.1H=2H), 6.86 (br s, 1H), 5.20 (q, J=6.9 Hz, 0.55H), 5.20 (q, J=6.9 Hz, 0.45H) (two rotamers 0.55H+0.45H=1H), 3.73 (t, J=5.9 Hz, 2H), 3.71 (s, 3H), 2.66 (t, J=5.9 Hz, 2H), 2.04 (d, J=6.9 Hz, 1.65H), 1.84 (d, J=6.9 Hz, 1.35H) (two rotamers 1.65H+1.35H=3H);MS (ES, m/z) 314, 316 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.83% | With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; | 5.1 Step 1: 4-(1-bromoethyl)-N,N-dimethylbenzamide: [00298] To a solution of 4-(1-bromoethyl)benzoic acid (350.00 mg, 1.53 mmol) in DMF (15.00 mL) was added HATU (865.83 mg, 2.30 mmol), DIEA (395.47 mg, 3.06 mmol, 534.42 μ.) and N-methylmethanamine (75.87 mg, 1.68 mmol). Then the reaction mixture was stirred at room temperature for 1 h. Then the reaction mixture was treated with water (100 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine (30 mL) , dried over Na2S04 and concentrated in vacuo. The crude product was purified by prep-TLC to give 4-(1-bromoethyl)-N,N-dimethyl-benzamide (15.00 mg, 58.56 μπιο, 3.83% yield) and most of a byproduct. ESI-MS (EI+, m/z): 256.1 [M+H]+. |
Tags: 113023-73-7 synthesis path| 113023-73-7 SDS| 113023-73-7 COA| 113023-73-7 purity| 113023-73-7 application| 113023-73-7 NMR| 113023-73-7 COA| 113023-73-7 structure
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