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[ CAS No. 18159-22-3 ]

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Chemical Structure| 18159-22-3
Chemical Structure| 18159-22-3
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Product Details of [ 18159-22-3 ]

CAS No. :18159-22-3 MDL No. :MFCD00894448
Formula : C12H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OGGDCEFWAMGBOB-UHFFFAOYSA-N
M.W :201.22 Pubchem ID :14985839
Synonyms :

Safety of [ 18159-22-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18159-22-3 ]

* 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 [ 18159-22-3 ]

[ 18159-22-3 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 18159-22-3 ]
  • 1-benzyl-1<i>H</i>-pyrrole-2-carbonyl azide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide
  • 2
  • [ 634-97-9 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In dimethyl sulfoxide
  • 3
  • [ 771-61-9 ]
  • [ 18159-22-3 ]
  • [ 942157-38-2 ]
YieldReaction ConditionsOperation in experiment
85% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;
  • 4
  • [ 4556-23-4 ]
  • [ 18159-22-3 ]
  • S-pyridin-4-yl 1-benzyl-1H-pyrrole-2-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;
  • 5
  • [ 18159-22-3 ]
  • [ 942157-19-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 2: 84 percent / n-BuLi / tetrahydrofuran / 3 h
  • 6
  • [ 18159-22-3 ]
  • n-butyl 4-(1-benzyl-1H-pyrrol-2-yl)-4-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C 2: 84 percent / n-BuLi / tetrahydrofuran / 3 h 3: 52 percent / samarium(II) iodide / tetrahydrofuran; H2O / 18 h / -78 °C
  • 7
  • [ 18159-22-3 ]
  • 3-(1-benzyl-1<i>H</i>-pyrrol-2-yl)-5-methoxymethyl-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: MeONa / 20 °C
  • 8
  • [ 18159-22-3 ]
  • 5-aminomethyl-3-(1-benzyl-1<i>H</i>-pyrrol-2-yl)-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: NaN3 / dimethylformamide / 70 °C 6.1: H2 / Pd/C / 20 °C
  • 9
  • [ 18159-22-3 ]
  • [ 869878-52-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane
  • 10
  • [ 18159-22-3 ]
  • 3-(1-benzyl-1<i>H</i>-pyrrol-2-yl)-5-methylaminomethyl-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: tetrahydrofuran / 65 °C
  • 11
  • [ 18159-22-3 ]
  • [ 869878-51-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (PhO)2PON3 2: Heating
  • 12
  • [ 18159-22-3 ]
  • [ 587869-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C 5.1: NaN3 / dimethylformamide / 70 °C
  • 13
  • [ 18159-22-3 ]
  • [ 869878-56-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (PhO)2PON3 2.1: Heating 3.1: n-BuLi / hexane / -78 °C 3.2: hexane 4.1: Et3N / CH2Cl2 / 20 °C
YieldReaction ConditionsOperation in experiment
2 1-(Phenylmethyl)-1H-Pyrrole-2-Carboxylic Acid The 5.0 g of oil was combined with 100 ml of ethanol (ethyl alcohol) in a 250 ml round bottom flask. The mixture was heated to reflux then sodium hydroxide (3.0 g) in 15 ml of water was added. The reaction refluxed for 2 hours and was then diluted with 50 ml water. The mixture was cooled in an ice-bath then acidified by addition of 5.0 g of malonic acid. The mixture was then extracted with diethylether in a 500 ml sepratory funnel. The ether layer was washed with water and saturated sodium chloride solution (brine). The ether layer was filtered through sodium sulfate and evaporated to dryness under reduced pressure to give 2.8 g of a brown crystalline solid. The solid was recrystallized from acetonitrile to give 1.3 g of white fluffy crystals of the title compound. mp=130° C. to 133° C. In like manner, by substituting the following starting materials for benzylamine above, and following the procedure in Example 2, the following compounds can be made:
2 1-(Phenylmethyl)-1H-Pyrrole-2-Carboxylic Acid The 5.0 g of oil was combined with 100 ml of ethanol (ethyl alcohol) in a 250 ml round bottom flask. The mixture was heated to reflux then sodium hydroxide (3.0 g) in 15 ml of water was added. The reaction refluxed for 2 hours and was then diluted with 50 ml water. The mixture was cooled in an ice-bath then acidified by addition of 5.0 g of malonic acid. The mixture was then extracted with diethylether in a 500 ml sepratory funnel. The ether layer was washed with water and saturated sodium chloride solution (brine). The ether layer was filtered through sodium sulfate and evaporated to dryness under reduced pressure to give 2.8 g of a brown crystalline solid. The solid was recrystallized from acetonitrile to give 1.3 g of white fluffy crystals of the title compound. mp =130° C. to 133° C. In like manner, by substituting the following starting materials for benzylamine above, and following the procedure in Example 2, the following compounds can be made:
  • 16
  • [ 15205-15-9 ]
  • [ 18159-22-3 ]
  • [ 1100566-04-8 ]
  • 17
  • [ 2051-97-0 ]
  • [ 124-38-9 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
80% With dimethylaluminum chloride In hexane; toluene at 20℃; for 3h; regioselective reaction;
  • 18
  • [ 2051-97-0 ]
  • [ 76-02-8 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-benzyl-1H-pyrrole; trifluoroacetyl chloride In diethyl ether for 24h; Inert atmosphere; Stage #2: With water; sodium hydroxide In ethanol for 5h; Reflux;
  • 19
  • [ 18159-22-3 ]
  • [ 51491-77-1 ]
YieldReaction ConditionsOperation in experiment
6.28 g With thionyl chloride In diethyl ether for 4h; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;
  • 20
  • [ 496-72-0 ]
  • [ 18159-22-3 ]
  • [ 1262222-14-9 ]
YieldReaction ConditionsOperation in experiment
80.14% With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h;
  • 21
  • [ 95-83-0 ]
  • [ 18159-22-3 ]
  • [ 1262222-16-1 ]
YieldReaction ConditionsOperation in experiment
79% With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h;
  • 22
  • [ 95-54-5 ]
  • [ 18159-22-3 ]
  • [ 1262222-13-8 ]
YieldReaction ConditionsOperation in experiment
75.4% With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h;
  • 23
  • [ 99-56-9 ]
  • [ 18159-22-3 ]
  • [ 1262222-15-0 ]
YieldReaction ConditionsOperation in experiment
67% With polyphosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 4h;
  • 24
  • [ 18159-22-3 ]
  • [ 1585225-84-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-ol / dichloromethane / 15.5 h / 0 - 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 15 h / 20 °C
  • 25
  • [ 89756-60-5 ]
  • [ 18159-22-3 ]
  • C14H17N3O3S [ No CAS ]
  • 26
  • [ 123476-57-3 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
With water; potassium hydroxide In methanol at 70℃; for 16h; 14 Intermediate 2-17.1-l3enzyl-1H-pyrrole-2-carboxylic acid Ethyl 1-benzyl-1H-pyrrole-2-carboxylate (458 mg,2.00 mmol), potassium hydroxide (1.12 g, 20.0 mmol), water(10 mE) and methanol (50 mE) were added to a 100-mEround-bottom flask fitted with a magnetic stir bar, thermometer and condenset The resulting solution was stirred for 16 h at 70° C. The pH of the solution was adjusted to 2 with hydrochloric acid (6.0 M aqueous) and the resulting solution was extracted with ethyl acetate (3x30 mE). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give 1 -benzyl- 1 Hpyrrole-2-carboxylic acid (Intermediate 2-17), which was used in the next step without purification. ECMS: (ESI) mlz 200 [M-H]
  • 27
  • [ 1193-62-0 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; water / methanol / 3 h / Reflux
  • 28
  • [ 18159-22-3 ]
  • 1-benzyl-1H-N-(2-guanidinoethyl)pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C 2: dichloromethane / 20 °C 3: N-iodo-succinimide; N-ethyl-N,N-diisopropylamine / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 29
  • [ 18159-22-3 ]
  • 1-Benzyl-1H-N-[2-(2,3-Di-Tert-Butoxycarbonyl)Guanidinoethyl]Pyrrole-2-Carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C 2: dichloromethane / 20 °C 3: N-iodo-succinimide; N-ethyl-N,N-diisopropylamine / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 30
  • [ 57260-73-8 ]
  • [ 18159-22-3 ]
  • 1-benzyl-1H-N-[2-(tert-butoxycarbonyl)aminoethyl]pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
248 mg With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 16h;
  • 31
  • [ 100-39-0 ]
  • [ 18159-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; water / methanol / 3 h / Reflux
  • 32
  • [ 18159-22-3 ]
  • 2,2,2-trifluoroethyl 3-(1-benzyl-1H-pyrrol-2-yl)-2-diazo-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 3: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 20 °C
  • 33
  • [ 18159-22-3 ]
  • 2,2,2-trifluoroethyl 3-(1-benzyl-1H-pyrrol-2-yl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
  • 34
  • [ 18159-22-3 ]
  • 2,2,2-trifluoroethyl 2-(1-benzyl-1H-pyrrol-2-yl)-5-ethoxy-4,5-dihydrofuran-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 3: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 20 °C 4: copper(II) hexafluoroacetylacetonate / dichloromethane / 16 h / 40 °C / Inert atmosphere
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