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CAS No. : | 906657-86-1 | MDL No. : | MFCD16140264 |
Formula : | C13H12BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 294.14 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
55% | With triethylamine In N,N-dimethyl-formamide at 20 - 80℃; for 18.5h; | A-1.4; B-1.4 4) To a solution of the compound 4 (88g, 300mmol), palladium acetate (13.4g, 60mmol) and l,3-bis(diphenylphosphino)propane (30.8g, SlCmmol) in dimethylformamide (660ml) wore added methanol (264ml) and triethylamine (210ml, l.5mol) at room temperature. The interior of a reaction vessel was replaced with carbon monoxide, and the material was stirred at room temperature for 30 minutes, and stirred at 80 degree for 18 hoxirs. A vessel to which ethyl acetate (1500ml), an aqueous saturated ammonium chloride solution (1500ml) and water (1500ml) had been added was stirred tinder ice-cooling, and tho reaction solution was added thereto. Precipitates were faltered, and washed with water (300ml), ethyl acetate (300ml) and diethyl ether (300ml) to obtain 5-benzyloxy^-hydroxy-δ-methyl-nicotimc acid methyl ester 5 (44 9g, 55%) as a colorless crystal.NMR GDMSO-d(,)δ: 2.06(3H, s), 3.72(3H, s), 5.02(2H, s), 7 33-7.42(5H, m), 8.07(1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With N-Bromosuccinimide; In acetonitrile; at 20℃; for 1.5h; | 3) Tho above compound 3 (I 29g, 599mmol) was suspended in acetonitrilo (1300ml), and N-bromosuccinic acid imide (I17g, 659mmol) was added, followed by stirring at room temperature for 90 minutes, Precipitated crystals were filtered, and washed with acetonitrilc and diethyl ether to obtain3-benzyloxy-5-bromo-2-methyl-pyridine-4-ol 4(154g, 88percent) as a colorless crystal. NMR. (DMSO-dbeta)delta: 2.06(3H, s), 5.04(2H, s), 7.32-7.42(5H, m), 8,03(1H, d, J=5.5Hz), 11.82(1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide / 0.25 h / 80 °C 1.2: 1 h 2.1: sodium hydroxide; ammonia / ethanol; water / 1 h / 90 °C 3.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 12.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation 13.1: trifluoroacetic acid / 1.58 h / 0 - 20 °C 13.2: 0 °C | ||
Multi-step reaction with 14 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 13.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation 14.1: trifluoroacetic acid / 1.58 h / 0 - 20 °C 14.2: 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 12.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation 13.1: hydrogen / palladium 10% on activated carbon / methanol; N,N-dimethyl-formamide / 20 h / 20 °C | ||
Multi-step reaction with 14 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 13.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation 14.1: hydrogen / palladium 10% on activated carbon / methanol; N,N-dimethyl-formamide / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C | ||
Multi-step reaction with 13 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C | ||
Multi-step reaction with 13 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2: 0.67 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2: 0.67 h / 130 °C 3: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2: 0.67 h / 130 °C 3: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4: 0.37 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C | ||
Multi-step reaction with 8 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C | ||
Multi-step reaction with 7 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C | ||
Multi-step reaction with 9 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux | ||
Multi-step reaction with 9 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C | ||
Multi-step reaction with 12 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C | ||
Multi-step reaction with 11 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 8.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 9.2: 1.5 h / Heating / reflux 10.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 11.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 12.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation | ||
Multi-step reaction with 13 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C 7.1: water; acetic acid; zinc / 1 h / Heating / reflux 7.2: 20 °C 8.1: manganese(IV) oxide / chloroform / 1.33 h / 20 - 60 °C 9.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C 10.2: 1.5 h / Heating / reflux 11.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C 12.1: potassium osmate(VI); sodium periodate; water / 1,4-dioxane / 2 h / 20 °C 13.1: acetic acid / dichloromethane / 0.58 h / 20 - 140 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triethylamine / palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C 2.1: 0.67 h / 130 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 0 - 20 °C 4.1: 0.37 h / 130 °C 5.1: methanol; sodium hydroxide; water / 0.67 h / 0 - 50 °C 5.2: 0 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; ammonia / ethanol; water / 1 h / 90 °C 2: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide / 0.25 h / 80 °C 1.2: 1 h 2.1: sodium hydroxide; ammonia / ethanol; water / 1 h / 90 °C 3.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C |