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Product Details of [ 168473-88-9 ]

CAS No. :168473-88-9 MDL No. :MFCD12031869
Formula : C9H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PPVXNRMIVXWQKP-UHFFFAOYSA-N
M.W : 244.09 Pubchem ID :19919763
Synonyms :

Safety of [ 168473-88-9 ]

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

Application In Synthesis of [ 168473-88-9 ]

* 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 [ 168473-88-9 ]

[ 168473-88-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 168473-88-9 ]
  • [ 141-97-9 ]
  • [ 1100261-88-8 ]
YieldReaction ConditionsOperation in experiment
32% With PPA at 110 - 120℃; for 1.16667h; 1.1 (1) Ethyl 8-bromo-4-hydroxy-2-methylquinoline-5- carboxylate A mixture of ethyl 3-amino-4-brorαobenzoate (89 g, 0.36 mol) and ethyl 3-oxobutanoate(141 g, 1.08 mol) was added to polyphosphoric acid (445 g) at 110-1200C over 1 h. After additional stirring at 1200C for 10 min, the mixture was cooled to 600C. After water, aq. NaOH and CHCl3 were added to the mixture, the mixture was filtered through celite. The filtrate was separated, and the organic layer was dried over Na2SU4, filtered and concentrated in vacuo. The residue was purified by flush column chromatography (silica gel C-200, CHCl3 / MeOH = 70 / 1 - 40 / 1) to give the title compound (35.5 g, 32 %) as a solid
  • 2
  • [ 168473-88-9 ]
  • [ 672-30-0 ]
  • [ 1402070-40-9 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: (3-bromophenyl)pentafluoro-λ6-sulfane With TurboGrignard In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran Inert atmosphere; Stage #3: 3-amino-4-bromobenzoic acid ethyl ester With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran for 1h; Inert atmosphere;
  • 3
  • [ 168473-88-9 ]
  • [ 619-42-1 ]
  • [ 121-46-0 ]
  • C24H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; triphenylphosphine; potassium iodide In N,N-dimethyl-formamide at 105℃; Schlenk technique; Inert atmosphere;
  • 4
  • [ 168473-88-9 ]
  • [ 618-89-3 ]
  • [ 121-46-0 ]
  • C24H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; triphenylphosphine; potassium iodide In N,N-dimethyl-formamide at 105℃; Schlenk technique; Inert atmosphere;
  • 5
  • [ 168473-88-9 ]
  • [ 59247-47-1 ]
  • [ 121-46-0 ]
  • C27H29NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; triphenylphosphine; potassium iodide In N,N-dimethyl-formamide at 105℃; Schlenk technique; Inert atmosphere;
  • 6
  • [ 168473-88-9 ]
  • [ 873-75-6 ]
  • [ 121-46-0 ]
  • C23H23NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; triphenylphosphine; potassium iodide In N,N-dimethyl-formamide at 105℃; Schlenk technique; Inert atmosphere;
  • 7
  • [ 168473-87-8 ]
  • [ 168473-88-9 ]
YieldReaction ConditionsOperation in experiment
98% With tin(II) chloride dihdyrate In ethyl acetate at 20℃; for 20h;
  • 8
  • [ 5798-75-4 ]
  • [ 168473-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 3.17 h / -8 - 0 °C 2: tin(II) chloride dihdyrate / ethyl acetate / 20 h / 20 °C
  • 9
  • potassium cyanide [ No CAS ]
  • [ 168473-88-9 ]
  • copper(l) cyanide [ No CAS ]
  • C10H8BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: 3-amino-4-bromobenzoic acid ethyl ester With hydrogenchloride; sodium nitrite In water at -2 - 0℃; Stage #2: potassium cyanide; copper(l) cyanide In water; toluene at 0 - 20℃;
  • 10
  • [ 168473-88-9 ]
  • [ 85107-55-7 ]
  • C17H16N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tris-(dibenzylideneacetone)dipalladium(0); potassium fluoride dihydrate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Schlenk technique;
  • 11
  • [ 168473-88-9 ]
  • C18H14N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / -2 - 0 °C 1.2: 0 - 20 °C 2.1: potassium fluoride dihydrate; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran / 1 h / Inert atmosphere; Reflux; Schlenk technique
  • 12
  • [ 168473-88-9 ]
  • [ 75-16-1 ]
  • 2-(3-amino-4-bromophenyl)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; toluene at 0℃; for 0.5h; 11 Intermediate 8, 2-(3-amino-4-bromophenyl)propan-2-ol Ethyl 3-amino-4-bromobenzoate was dissolved in dry THF and cooled to 0°C. 6 eq. 1.4M methyl magnesium bromide in THF/toluene (1/3) were added and the mixture stirred for 30 min at 0°C. The reaction mix was quenched by addition of NH4CI sat. aq. and extracted with ethyl acetate. The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography.
In tetrahydrofuran; toluene at 0℃; for 0.5h; 11 Example 11 Intermediate 8, 2-(3-amino-4-bromophenyl)propan-2-ol. Ethyl 3-amino-4- bromobenzoate was dissolved in dry THF and cooled to 0°C. 6 eq. 1.4M methyl magnesium bromide in THF/toluene (1/3) were added and the mixture stirred for 30 min at 0°C. The reaction mix was quenched by addition of NH4CI sat. aq. and extracted with ethyl acetate. The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography.
In tetrahydrofuran; toluene at 0℃; for 0.5h; 11 Example 11 Intermediate 8, 2-(3-amino-4-bromophenyl)propan-2-ol. Ethyl 3-amino-4- bromobenzoate was dissolved in dry THF and cooled to 0°C. 6 eq. 1.4M methyl magnesium bromide in THF/toluene (1/3) were added and the mixture stirred for 30 min at 0°C. The reaction mix was quenched by addition of NH4CI sat. aq. and extracted with ethyl acetate. The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography.
  • 13
  • [ 168473-88-9 ]
  • ethyl 8-bromo-4-oxo-1H-quinoline-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C
Multi-step reaction with 2 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C
  • 14
  • [ 168473-88-9 ]
  • ethyl 4,8-dibromoquinoline-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C
Multi-step reaction with 3 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C
  • 15
  • [ 168473-88-9 ]
  • 14-bromo-19-[(4-methoxyphenyl)methyl]-18,19-diazatricyclododeca-5(12),6(14),7(13),8(18),15-pentaen-17-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C
Multi-step reaction with 4 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C
  • 16
  • [ 168473-88-9 ]
  • tert-butyl 4-(17-oxo-20,21-diazatricyclododeca-3,5(13),6(20),11(14),12(15)-pentaen-12-yl)-3,6-dihydro-2H-pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C
Multi-step reaction with 6 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C
  • 17
  • [ 168473-88-9 ]
  • tert-butyl 4-(3-oxo-2,9-diazatricyclo[6.3.1.04,12]dodeca-4(12),5,7-trien-7-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C 7: hydrogen; palladium hydroxide on carbon / ethyl acetate / 16 h / 20 °C
  • 18
  • [ 168473-88-9 ]
  • tert-butyl 4-(17-oxo-20,21-diazatricyclododeca-3,5(13),6(20),11(15),12(14)-pentaen-11-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C 7: hydrogen; palladium hydroxide on carbon / ethyl acetate / 16 h / 20 °C 8: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 0 - 20 °C
Multi-step reaction with 7 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C
  • 19
  • [ 168473-88-9 ]
  • tert-butyl 4-[28-(2,6-dioxo-3-piperidyl)-21-oxo-25,28-diazatricyclododeca-3,5(15),6(25),13(17),14(16)-pentaen-13-yl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C 7.1: hydrogen; palladium hydroxide on carbon / ethyl acetate / 16 h / 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 0 - 20 °C 9.1: lithium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 5 - 20 °C / Inert atmosphere 9.2: 16 h / 90 °C / Inert atmosphere
Multi-step reaction with 8 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8: lithium tert-butylate / N,N-dimethyl-formamide / 16 h / 0 - 90 °C
  • 20
  • [ 168473-88-9 ]
  • 3-[18-oxo-10-(4-piperidyl)-20,23-diazatricyclododeca-2(12),3(20),10(14),11(13)-pentaen-23-yl]piperidine-2,6-dione hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C 7.1: hydrogen; palladium hydroxide on carbon / ethyl acetate / 16 h / 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 0 - 20 °C 9.1: lithium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 5 - 20 °C / Inert atmosphere 9.2: 16 h / 90 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane
Multi-step reaction with 9 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8: lithium tert-butylate / N,N-dimethyl-formamide / 16 h / 0 - 90 °C 9: hydrogenchloride / 1,4-dioxane / 3 h / 0 °C
  • 21
  • [ 168473-88-9 ]
  • 3-[21-[1-[(3-morpholinosulfonylphenyl)methyl]-4-piperidyl]-29-oxo-31,35-diazatricyclododeca-3(21),4(22),5(23),6(31),24-pentaen-35-yl]piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: Cs2CO3; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 90 °C 7.1: hydrogen; palladium hydroxide on carbon / ethyl acetate / 16 h / 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 0 - 20 °C 9.1: lithium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 5 - 20 °C / Inert atmosphere 9.2: 16 h / 90 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane 11.1: di-n-butyldichlorostannane; triethylamine / tetrahydrofuran / 1 h / 60 °C
Multi-step reaction with 10 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7.1: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8.1: lithium tert-butylate / N,N-dimethyl-formamide / 16 h / 0 - 90 °C 9.1: hydrogenchloride / 1,4-dioxane / 3 h / 0 °C 10.1: di-n-butyldichlorostannane; triethylamine / tetrahydrofuran / 1 h / 60 °C 10.2: 12 h / 80 °C
  • 22
  • [ 168473-88-9 ]
  • 8-bromopyrrolo[2,3,4-de]quinolin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ethanol / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C
Multi-step reaction with 5 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C
  • 23
  • [ 168473-88-9 ]
  • 3-(8-bromo-5-oxopyrrolo[2,3,4-de]quinolin-4(5H)-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 60 °C
Multi-step reaction with 6 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0 - 60 °C
  • 24
  • [ 168473-88-9 ]
  • 16-oxo-N-(1-phenylethyl)-19,20-diazatricyclododeca-6(11),7(12),8(13),9(19),14-pentaene-12-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: 1,3-bis-(diphenylphosphino)propane / dimethyl sulfoxide; <i>tert</i>-butyl alcohol / 0.25 h / Inert atmosphere 6.2: 12 h / 100 °C / 3102.97 Torr
  • 25
  • [ 168473-88-9 ]
  • 27-(2,6-dioxo-3-piperidyl)-20-oxo-N-(1-phenylethyl)-24,27-diazatricyclododeca-6,8(15),9(24),13(16),14(17)-pentaene-14-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 5.5 h / 0 - 70 °C 6.1: 1,3-bis-(diphenylphosphino)propane / dimethyl sulfoxide; <i>tert</i>-butyl alcohol / 0.25 h / Inert atmosphere 6.2: 12 h / 100 °C / 3102.97 Torr 7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 5 - 20 °C 7.2: 1 h / 70 °C
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: 1,3-bis-(diphenylphosphino)propane; palladium diacetate / <i>tert</i>-butyl alcohol; dimethyl sulfoxide / 12 h / 100 °C / 3102.97 Torr / Inert atmosphere 7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 5 - 20 °C 7.2: 1 h / 0 - 70 °C
  • 26
  • [ 168473-88-9 ]
  • [ 15568-85-1 ]
  • ethyl 4-bromo-3-[((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In ethanol at 80℃; 62.1 Step 1: To a well stirred solution of ethyl 3-amino-4-bromo-benzoate (20 g, 81.94 mmol) in ethanol (100 mL) was added 5-(methoxymethylene)-2,2-dimethyl-l,3-dioxane-4,6- dione (12.00 g, 64.46 mmol) and the reaction mixture was heated at 80 °C overnight. After completion, the solvent was removed under reduced pressure to obtain crude residue which was then washed with pentane followed by 50% Et2O/Pentane to afford ethyl 4-bromo-3-[(2,2- dimethyl-4,6-dioxo-l,3-dioxan-5-ylidene)methylamino]benzoate (25 g, 50.23 mmol, 61% yield) as yellow solid. XH NMR (400 MHz, DMSO-tL) 6 11.51 (d, J= 13.8 Hz, 1H), 8.74 (t, J = 7.2 Hz, 1H), 8.22 (d, J= 1.16 Hz, 1H), 7.91 (d, J = 8.32 Hz, 1H), 7.74-7.71 (m, 1H), 4.39-4.33 (q, 2H), 1.7 (s, 6H), 1.34 (t, J= 7.08 Hz, 1H).
61% In ethanol at 80℃; for 12h; 51.1 Step 1: To a well stirred solution of ethyl 3-amino-4-bromo-benzoate (20 g, 81.94 mmol) in ethanol (100 mL) was added 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6- dione (12.00 g, 64.46 mmol) and the reaction mixture was heated at 80 °C overnight. After completion, the solvent was removed under reduced pressure to obtain crude residue which was then washed with pentane followed by 50% Et2O/Pentane to afford ethyl 4-bromo-3-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]benzoate (25 g, 50.23 mmol, 61% yield) as yellow solid. 1H NMR (400 MHz, DMSO-tL) 6 11.51 (d, J= 13.8 Hz, 1H), 8.74 (t, J = 7.2 Hz, 1H), 8.22 (d, J= 1.16 Hz, 1H), 7.91 (d, J = 8.32 Hz, 1H), 7.74-7.71 (m, 1H), 4.39-4.33 (q, 2H), 1.7 (s, 6H), 1.34 (t, J= 7.08 Hz, 1H).
  • 27
  • [ 168473-88-9 ]
  • C19H22N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: n-butyllithium / diethyl ether / 0.5 h / -78 °C 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
  • 28
  • [ 168473-88-9 ]
  • 4-(2,6-dioxopiperidin-3-yl)-5-oxo-N-((3R,5S)-1,3,5-trimethylpiperidin-4-yl)-4,5-dihydropyrrolo[2,3,4-de]qninoline-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: n-butyllithium / diethyl ether / 0.5 h / -78 °C 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 8.1: sodium hydride / mineral oil; tetrahydrofuran / 0 °C 8.2: 0 - 20 °C
  • 29
  • [ 168473-88-9 ]
  • 3-(8-fluoro-5-oxopyrrolo[2.3.4-de]quinolin-4(5H)-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0 - 60 °C 7.1: caesium fluoride; [(AlPhosPd)2*COD] / toluene / 20 °C / Inert atmosphere
  • 30
  • [ 168473-88-9 ]
  • C21H20N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: 1-methyl-pyrrolidin-2-one / 12 h / 100 °C / Sealed tube
  • 31
  • [ 168473-88-9 ]
  • C26H25N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: 1-methyl-pyrrolidin-2-one / 12 h / 100 °C / Sealed tube 7.1: sodium hydride / mineral oil; tetrahydrofuran / 5 - 20 °C 7.2: 1 h / 0 - 70 °C
  • 32
  • [ 168473-88-9 ]
  • C19H15N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: 1,3-bis-(diphenylphosphino)propane; palladium diacetate / <i>tert</i>-butyl alcohol; dimethyl sulfoxide / 12 h / 100 °C / 3102.97 Torr / Inert atmosphere
  • 33
  • [ 168473-88-9 ]
  • tert-butyl 4-hydroxy-4-(16-oxo-20,21-diazatricyclododeca-3,5(13),6(20),11(14),12(15)-pentaen-12-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: n-butyllithium; phenyllithium / tetrahydrofuran; dibutyl ether / 1 h / -78 - -40 °C / Inert atmosphere 6.2: 16 h / -78 - 20 °C
  • 34
  • [ 168473-88-9 ]
  • tert-butyl 4-fluoro-4-(16-oxo-20,21-diazatricyclododeca-3(11),4(12),5(13),6(20),14-pentaen-12-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: n-butyllithium; phenyllithium / tetrahydrofuran; dibutyl ether / 1 h / -78 - -40 °C / Inert atmosphere 6.2: 16 h / -78 - 20 °C 7.1: diethylamino-sulfur trifluoride / dichloromethane / 4 h / -78 - 20 °C
  • 35
  • [ 168473-88-9 ]
  • C18H19N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl acetamide / 2 h / 25 °C / Inert atmosphere 6.2: 16 h / 100 °C / Inert atmosphere
  • 36
  • [ 168473-88-9 ]
  • C13H11N3O*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl acetamide / 2 h / 25 °C / Inert atmosphere 6.2: 16 h / 100 °C / Inert atmosphere 7.1: dichloromethane / 2 h / 0 - 20 °C
  • 37
  • [ 168473-88-9 ]
  • 8-(1-benzylazetidin-3-yl)pyrrolo[2,3,4-de]quinolin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl acetamide / 2 h / 25 °C / Inert atmosphere 6.2: 16 h / 100 °C / Inert atmosphere 7.1: dichloromethane / 2 h / 0 - 20 °C 8.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 0 - 20 °C
  • 38
  • [ 168473-88-9 ]
  • C25H22N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl acetamide / 2 h / 25 °C / Inert atmosphere 6.2: 16 h / 100 °C / Inert atmosphere 7.1: dichloromethane / 2 h / 0 - 20 °C 8.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 0 - 20 °C 9.1: lithium tert-butylate / N,N-dimethyl-formamide / 20 h / 0 - 80 °C / Sealed tube
  • 39
  • [ 168473-88-9 ]
  • C15H15N3O*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C
  • 40
  • [ 168473-88-9 ]
  • C22H21N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7.1: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8.1: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C 9.1: triethylamine; glacial acetic acid / methanol; dichloromethane / 4 h / 20 °C / pH Ca. 7 / Inert atmosphere 9.2: 12 h / 0 - 60 °C
  • 41
  • [ 168473-88-9 ]
  • 3-(8-(1-benzylpiperidin-4-yl)-5-oxopyrrolo[2,3,4-de]quinolin-4(5H)-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 16 h / 100 °C 7.1: hydrogen; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C 8.1: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C 9.1: triethylamine; glacial acetic acid / methanol; dichloromethane / 4 h / 20 °C / pH Ca. 7 / Inert atmosphere 9.2: 12 h / 0 - 60 °C 10.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 5 - 20 °C 10.2: 1 h / 0 - 70 °C
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0 - 60 °C 7.1: 2-dicyclohexylphosphino-1,1'-biphenyl; tripotassium phosphate tribasic; palladium diacetate / toluene; lithium hydroxide monohydrate / 20 h / 100 °C / Sealed tube; Inert atmosphere
  • 42
  • [ 168473-88-9 ]
  • C26H24N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0 - 60 °C 7.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
  • 43
  • [ 168473-88-9 ]
  • 4-(2,6-bis(benzyloxy)pyridin-3-yl)-8-bromopyrrolo[2,3,4-de]quinolin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: N<SUB>1</SUB>,N<SUB>2</SUB>-dimethylethane-1,2-diamine; potassium carbonate; copper (I) iodide / 1,4-dioxane / 110 °C / Sealed tube
  • 44
  • [ 168473-88-9 ]
  • 3-(8-(1H-indol-3-yl)-5-oxopyrrolo[2,3,4-de]quinolin-4(5H)-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0 - 60 °C 7.1: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; L-Aspartic acid; tripotassium phosphate tribasic / tetrahydrofuran / 24 h / 100 °C / Sealed tube
  • 45
  • [ 168473-88-9 ]
  • 8-vinylpyrrolo[2,3,4-de]quinolin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere
  • 46
  • [ 168473-88-9 ]
  • 5-oxo-4,5-dihydropyrrolo[2,3,4-de]quinoline-8-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere 7: sodium (meta)periodate; osmium(VIII)-tetroxide / lithium hydroxide monohydrate; tetrahydrofuran / 1.33 h / 20 °C
  • 47
  • [ 168473-88-9 ]
  • (E)-2-methyl-N-((5-oxo-4,5-dihydropyrrolo[2,3,4-de]quinolin-8-yl)methylene)propane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: ethanol / 12 h / 80 °C 2: diphenylether / 0.33 h / 260 °C 3: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere 7: sodium (meta)periodate; osmium(VIII)-tetroxide / lithium hydroxide monohydrate; tetrahydrofuran / 1.33 h / 20 °C 8: iodine / dichloromethane / 0.33 h / Milling
  • 48
  • [ 168473-88-9 ]
  • N-((S)-2-(2-(hydroxymethyl)phenyl)-1-(5-oxo-4,5-dihydropyrrolo[2,3,4-de]quinolin-8-yl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere 7.1: sodium (meta)periodate; osmium(VIII)-tetroxide / lithium hydroxide monohydrate; tetrahydrofuran / 1.33 h / 20 °C 8.1: iodine / dichloromethane / 0.33 h / Milling 9.1: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 9.2: 0.25 h / 20 °C 9.3: 12 h / -65 °C
  • 49
  • [ 168473-88-9 ]
  • (S)-8-(1,2,3,4-tetrahydroisoquinoiin-3-yl)pyrrolo[2,3,4-de]quinolin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere 7.1: sodium (meta)periodate; osmium(VIII)-tetroxide / lithium hydroxide monohydrate; tetrahydrofuran / 1.33 h / 20 °C 8.1: iodine / dichloromethane / 0.33 h / Milling 9.1: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 9.2: 0.25 h / 20 °C 9.3: 12 h / -65 °C 10.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 0 °C 10.2: 4 h / 0 - 50 °C 10.3: 10 h / 20 °C
  • 50
  • [ 168473-88-9 ]
  • tert-butyl (S)-3-(5-oxo-4,5-dihydropyrrolo[2,3,4-de]quinolin-8-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: ethanol / 12 h / 80 °C 2.1: diphenylether / 0.33 h / 260 °C 3.1: phosphorus oxytribromide / dichloromethane / 3 h / 140 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 80 °C 5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 0 - 70 °C 6.1: tetrakis-(triphenylphosphine)-palladium; triphenylphosphine / toluene / 16 h / 110 °C / Inert atmosphere 7.1: sodium (meta)periodate; osmium(VIII)-tetroxide / lithium hydroxide monohydrate; tetrahydrofuran / 1.33 h / 20 °C 8.1: iodine / dichloromethane / 0.33 h / Milling 9.1: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 9.2: 0.25 h / 20 °C 9.3: 12 h / -65 °C 10.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 0 °C 10.2: 4 h / 0 - 50 °C 10.3: 10 h / 20 °C 11.1: 1,4-dioxane; dichloromethane / 5.17 h / 20 °C
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