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[ CAS No. 906657-86-1 ] {[proInfo.proName]}

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Chemical Structure| 906657-86-1
Chemical Structure| 906657-86-1
Structure of 906657-86-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 906657-86-1 ]

CAS No. :906657-86-1 MDL No. :MFCD16140264
Formula : C13H12BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 294.14 Pubchem ID :-
Synonyms :

Safety of [ 906657-86-1 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 906657-86-1 ]

* 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.

  • Downstream synthetic route of [ 906657-86-1 ]

[ 906657-86-1 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 67-56-1 ]
  • [ 906657-86-1 ]
  • [ 201230-82-2 ]
  • [ 906657-87-2 ]
YieldReaction ConditionsOperation 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).
  • 2
  • [ 61160-18-7 ]
  • [ 1421314-64-8 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 118-71-8 ]
  • [ 906657-86-1 ]
YieldReaction ConditionsOperation 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
  • 4
  • [ 906657-86-1 ]
  • 9-hydroxy-2-(2-methoxy-ethyl)-1,8-dioxo-1,8-dihydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 5
  • [ 906657-86-1 ]
  • 9-hydroxy-2-(2-methoxy-ethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 6
  • [ 906657-86-1 ]
  • C23H27FN4O4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 906657-86-1 ]
  • C22H25FN4O4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 906657-86-1 ]
  • [ 906658-57-9 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 906657-86-1 ]
  • [ 906657-88-3 ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 906657-86-1 ]
  • [ 906657-89-4 ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 906657-86-1 ]
  • [ 906657-90-7 ]
YieldReaction ConditionsOperation 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
  • 12
  • [ 906657-86-1 ]
  • [ 906657-94-1 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 906657-86-1 ]
  • [ 906657-92-9 ]
YieldReaction ConditionsOperation 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
  • 14
  • [ 906657-86-1 ]
  • [ 906658-58-0 ]
YieldReaction ConditionsOperation 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
  • 15
  • [ 906657-86-1 ]
  • [ 906657-96-3 ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 906657-86-1 ]
  • [ 906657-98-5 ]
YieldReaction ConditionsOperation 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
  • 17
  • [ 906657-86-1 ]
  • [ 906657-97-4 ]
YieldReaction ConditionsOperation 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
  • 18
  • [ 906657-86-1 ]
  • [ 906657-99-6 ]
YieldReaction ConditionsOperation 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
  • 19
  • [ 906657-86-1 ]
  • [ 906657-93-0 ]
YieldReaction ConditionsOperation 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
  • 20
  • [ 61049-69-2 ]
  • [ 906657-86-1 ]
YieldReaction ConditionsOperation 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
  • 21
  • [ 100-39-0 ]
  • [ 906657-86-1 ]
YieldReaction ConditionsOperation 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
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