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[ CAS No. 1190321-59-5 ] {[proInfo.proName]}

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Chemical Structure| 1190321-59-5
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Product Details of [ 1190321-59-5 ]

CAS No. :1190321-59-5 MDL No. :MFCD12963482
Formula : C7H4BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GRDJQIJVCMSPFF-UHFFFAOYSA-N
M.W :231.48 Pubchem ID :53412942
Synonyms :

Safety of [ 1190321-59-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1190321-59-5 ]

* 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 [ 1190321-59-5 ]

[ 1190321-59-5 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 1207625-24-8 ]
  • [ 1190321-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 4 h / 20 °C / Cooling 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / Reflux
  • 2
  • [ 1207625-25-9 ]
  • [ 1190321-59-5 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Reflux; 78.5 The compound obtained in the above Step 4 (0.95 g) was dissolved in tetrahydrofuran (15 ml). Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran) (5.5 ml) was added and the mixture was heated under reflux for 1.5 hours. The reaction solution was cooled to room temperature and then tetrahydrofuran was distilled off. The residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting solid was collected by filtration from chloroform to give the title compound (0.4 g).MS (ESI) m/z: 231 (M+H)+.1H-NMR (DMSO-d6) δ: 6.47-6.49 (1H, m), 7.59-7.59 (1H, m), 8.40-8.42 (1H, m), 12.04-12.06 (1H, m).
  • 3
  • [ 1190321-59-5 ]
  • 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.605 g With chlorosulfonic acid In acetonitrile at 0 - 80℃; for 12h; C.C.14 C.14. Synthesis of 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride (1188) XII-14 : To a solution of 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (0.50 g, 2.16 mmol) in CH3CN (10 mL) was added CIS03H (5 mL) at 0°C and the reaction mixture was heated at 80°C for 12h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was poured in to ice-H20 (150 mL), the precipitate was filtered and dried in vacuum to afford 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride (0.605 g crude) as a brown solid. (1192) This compound was used as such for the next reaction without further purification. (1193) Basic LCMS Method 2 (ES ): 309 (M-H)- (corresponding sulfonic acid), 97 % purity.
  • 4
  • [ 1190321-59-5 ]
  • 5-bromo-6-chloro-N-[6-(2,2-difluoroethoxy)-5-fluoro-2-methoxypyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chlorosulfonic acid / acetonitrile / 12 h / 0 - 80 °C 2: dmap; pyridine / 2 h / 90 °C
  • 5
  • [ 1190321-59-5 ]
  • [ 98-09-9 ]
  • 1-(benzenesulfonyl)-5-bromo-6-chloropyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; 226.1 Step-1 : Synthesis of l-(benzenesulfonyl)-5-bromo-6-chloropyrrolo[2,3-b]pyridine To a solution of NaH (54.4 mg, 2.26 mmol) in THF (3.0 mL) was added 5-bromo-6- chloro-lH-pyrrolo[2,3-b]pyridine (350 mg, 1.51 mmol) in small portions at 0 °C. The resulting mixture was stirred at 0 °C for 15 minutes. A solution of benzenesulfonyl chloride (400 mg, 2.26 mmol) in THF (3.0 mL) was then added to the above mixture dropwise at 0 °C. The resulting mixture was then stirred at room temperature for 1 hour under nitrogen. The resulting mixture was quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with 0-20% ethyl acetate in petroleum ether to afford the title compound (500 mg, 88%) as a white solid.
  • 6
  • [ 1190321-59-5 ]
  • 1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridine-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
  • 7
  • [ 1190321-59-5 ]
  • 1-(benzenesulfonyl)-6-(2-methoxyphenyl)pyrrolo[2,3-b]pyridine-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 8
  • [ 1190321-59-5 ]
  • 1-(benzenesulfonyl)-N-[5-[(5-chloropyridin-2-yl)methoxy]-1,3,4-thiadiazol-2-yl]-6-(2-methoxyphenyl)pyrrolo[2,3-b]pyridine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere 4.1: 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate / N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C / Inert atmosphere
  • 9
  • [ 1190321-59-5 ]
  • N-[5-[(5-chloropyridin-2-yl)methoxy]-1,3,4-thiadiazol-2-yl]-6-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere 4.1: 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate / N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C / Inert atmosphere 5.1: sodium hydroxide / methanol / 0.5 h / 50 °C
  • 10
  • [ 1190321-59-5 ]
  • 4-(5-((4-chloro-2-fluorophenyl)amino)-1-(ethylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-6-yl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3.1: potassium carbonate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium / water; 1,4-dioxane / 2 h / 60 °C / Microwave irradiation 4.1: trifluoroacetic acid / dichloromethane / 20 °C 5.1: sodium hydride / tetrahydrofuran / 0.5 h / Cooling with ice 5.2: 0 - 20 °C
  • 11
  • [ 1190321-59-5 ]
  • 6-chloro-N-(4-chloro-2-fluorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere
  • 12
  • [ 1190321-59-5 ]
  • 4-(5-((4-chloro-2-fluorophenyl)amino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3: potassium carbonate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium / water; 1,4-dioxane / 2 h / 60 °C / Microwave irradiation
  • 13
  • [ 1190321-59-5 ]
  • 4-(5-((4-chloro-2-fluorophenyl)amino)-1H-pyrrolo[2,3-b]pyridin-6-yl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3: potassium carbonate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium / water; 1,4-dioxane / 2 h / 60 °C / Microwave irradiation 4: trifluoroacetic acid / dichloromethane / 20 °C
  • 14
  • [ 1190321-59-5 ]
  • 7-(5-((4-chloro-2-fluorophenyl)amino)-1-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-6-yl)-2,5-dimethyl-2,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 110 °C / Microwave irradiation; Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 20 °C 5.1: water; ethanol; sodium carbonate / 20 h / 20 °C 6.1: sodium hydride / tetrahydrofuran / 0.5 h / Cooling with ice 6.2: 20 °C
  • 15
  • [ 1190321-59-5 ]
  • 7-(5-((4-chloro-2-fluorophenyl)amino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-2,5-dimethyl-2,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 110 °C / Microwave irradiation; Inert atmosphere
  • 16
  • [ 1190321-59-5 ]
  • 7-(5-((4-chloro-2-fluorophenyl)amino)-1-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-2,5-dimethyl-2,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 110 °C / Microwave irradiation; Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 20 °C
  • 17
  • [ 1190321-59-5 ]
  • 7-(5-((4-chloro-2-fluorophenyl)amino)-1H-pyrrolo[2,3-b]pyridin-6-yl)-2,5-dimethyl-2,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 110 °C / Microwave irradiation; Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 20 °C 5: water; ethanol; sodium carbonate / 20 h / 20 °C
  • 18
  • [ 1190321-59-5 ]
  • 7-(5-((4-chloro-2-fluorophenyl)amino)-1-(ethylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-2,5-dimethyl-2,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / N,N-dimethyl-formamide / 105 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate / 6 h / 110 °C / Microwave irradiation; Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 20 °C 5.1: water; ethanol; sodium carbonate / 20 h / 20 °C 6.1: sodium hydride / tetrahydrofuran / 0.67 h / Cooling with ice 6.2: 20 °C
  • 19
  • [ 1190321-59-5 ]
  • [ 76513-69-4 ]
  • 5-bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.32% Stage #1: 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2.25h; 1-16 Synthesis of 5-bromo-6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[2,3- b]pyridine: Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (6.00 g, 25.920 mmol, 1.00 equiv), DMF (100.00 mL). This was followed by the addition of NaH (2.00 g, 60%, 2 equiv), in portions at 0 degrees C in 10 min. To this was added SEM-Cl (6.48 g, 38.867 mmol, 1.50 equiv) at 0 degrees C in 15 min. The resulting solution was stirred for 2 hr at room temperature. The reaction was then quenched by the addition of 10 mL of H2O at 0 degrees C. The resulting solution was diluted with 500 mL of H2O. The resulting solution was extracted with 3x100 mL of ethyl acetate. The resulting mixture was washed with 2 x100 ml of H2O. The resulting mixture was washed with 1x100 mL of NaCl(aq.). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (10:1). This resulted in 8 g (85.32%) of 5-bromo-6- chloro-1-[[2-(trimethylsilyl)ethoxy] methyl]pyrrolo[2,3-b]pyridine as a light yellow solid. LC-MS-14: (ES, m/z): 361 [M+H].
120 mg With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 4.1; 7.1 The first step: 5-bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (4-2) Under the protection of nitrogen, the compound 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (4-1) (100mg) was dissolved in THF (20mL), and the temperature was cooled to 0 in an ice bath. Subsequently, the compound SEM-Cl (87 mg) was dissolved in THF (3 mL) and added dropwise to the reaction system, gradually warming to room temperature and stirring overnight. It was quenched by adding saturated ammonium chloride solution, extracted with ethyl acetate (30 mL), the organic phase was dried over anhydrous sodium sulfate, filtered, the filtrate was removed from the solvent under vacuum, and the residue was passed through a silica gel column (PE:EA=10:1) Purification gave the target compound 4-2 (120 mg).
  • 20
  • [ 183208-35-7 ]
  • [ 1190321-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 0.5 h / 0 °C 2: 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / acetonitrile / 6 h / 70 °C
  • 21
  • 5-bromo-7-oxido-1H-pyrrolo[2,3-b]pyridin-7-ium [ No CAS ]
  • [ 1190321-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 6 h / 70 °C
  • 22
  • benzyl 5-bromo-6-chloropyrrolo[2,3-b]pyridine-1-carboxylate [ No CAS ]
  • [ 1190321-59-5 ]
YieldReaction ConditionsOperation in experiment
61.96% With potassium carbonate In acetonitrile at 70℃; for 6h; 1-16 Synthesis of 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine: Into a 500-mL round- bottom flask, was placed benzyl 5-bromo-6-chloropyrrolo[2,3-b]pyridine-1-carboxylate (13.00 g, 35.557 mmol, 1.00 equiv), CH3CN (150.00 mL), K2CO3 (14.74 g, 106.653 mmol, 3.00 equiv). The resulting solution was stirred for 6 hr at 70 degrees C in an oil bath. The resulting mixture was concentrated. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:3). This resulted in 6 g (61.96%) of 5-bromo-6- chloro-1H-pyrrolo[2,3-b]pyridine as a brown solid. LC-MS-13: (ES, m/z): 231 [M+H].
  • 23
  • [ 1190321-59-5 ]
  • N-(6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[2,3-b]pyridin-5-yl)pyridin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 2.25 h / 0 - 20 °C 2.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere
  • 24
  • [ 1190321-59-5 ]
  • 14-[[2-(trimethylsilyl)ethoxy]methyl]-4,8,14,16-tetraazatetracyclo[7.7.0.0^[2,7].0^[11,15]]hexadeca-1(16),2(7),3,5,9,11(15),12-heptaene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 2.25 h / 0 - 20 °C 2.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 3.1: potassium carbonate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / N,N-dimethyl acetamide / 16 h / 130 °C / Inert atmosphere
  • 25
  • [ 1190321-59-5 ]
  • 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl]piperazin-1-yl)-N-(4-[[(2S)-1,4-dioxan-2-ylmethyl]amino]-3-nitrobenzenesulfonyl)-2-(14-[[2-(trimethylsilyl)ethoxy]methyl]-4,8,14,16-tetraazatetracyclo[7.7.0.0^[2,7].0^[11,15]]hexadeca-1(16),2(7),3,5 9,11(15),12-heptaen-8-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 2.25 h / 0 - 20 °C 2.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 3.1: potassium carbonate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / N,N-dimethyl acetamide / 16 h / 130 °C / Inert atmosphere 4.1: potassium carbonate; copper(l) iodide; N,N-diethylsalicylamide / N,N-dimethyl acetamide / 14 h / 10 °C / Inert atmosphere
  • 26
  • [ 1190321-59-5 ]
  • 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl]piperazin-1-yl)-N-(4-[[(2S)-1,4-dioxan-2-ylmethyl]amino]-3-nitrobenzenesulfonyl)-2-[4,8,14,16-tetraazatetracyclo[7.7.0.0^[2,7].0^[11,15]]hexadeca-1(16),2(7),3,5,9,11(15),12-heptaen-8-yl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 2.25 h / 0 - 20 °C 2.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 3.1: potassium carbonate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / N,N-dimethyl acetamide / 16 h / 130 °C / Inert atmosphere 4.1: potassium carbonate; copper(l) iodide; N,N-diethylsalicylamide / N,N-dimethyl acetamide / 14 h / 10 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ethylenediamine / tetrahydrofuran / 24 h / 70 °C
  • 27
  • [ 1190321-59-5 ]
  • [ 3863-11-4 ]
  • 6-chloro-N-(3,4-difluorophenyl)-1H-pyrrolo[2,3-b]pyridin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine With potassium-t-butoxide; tBuXPhos Pd G4; di-tertbutyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In <i>tert</i>-butyl alcohol at 30℃; Stage #2: 3,4-difluoro-phenylamine In <i>tert</i>-butyl alcohol at 30℃; 4.1 Weighed 5-bromo-6-chloro-lH-pyrrolo[2,3-b]pyridine (944.5 mg, 4.080 mmol), t-butyl XPhos Palladacycle generation 4 (362 mg, 0.4052 mmol), potassium t-butoxide (1.372 g, 12.23 mmol), and ditert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl] phosphane (362 mg, 0.8525 mmol) into a 40 mL vial. Added t-butanol (21 mL) and wanned in a 30 °C heating block. Degassed with Nz for 1 minute. Added 3,4-difluoroaniline (425 pL, 4.286 mmol) and stirred at 30 °C overnight. Diluted with dichloromethane (100 mL). Washed the organics with 0.5 M HC1 aqueous solution (50 mL), and washed the aqueous phase with 10% methanol in Agent Ref. 10275.0199-00304 dichloromethane (100 mL). Combined the organic phases and dried over NaiSCU, filtered, added celite and evaporated the solvent under reduced pressure. Purification by silica gel chromatography on 80 g of Silica in a gold cartridge: (Gradient: 0-100 % ethyl acetate in heptane). Concentrated the desired fractions to dryness under reduced pressure to yield the product as a white solid, 6-chloro-N-(3,4-difluorophenyl)-lH-pyrrolo[2,3-b]pyridin-5-amine (620 mg, 53%) 1H NMR (300 MHz, DMSO-d6) 8 11.82 (s, 1H), 7.95 (s, 1H), 7.84 (s, 1H), 7.55 - 7.46 (m, 1H), 7.24 - 7.11 (m, 1H), 6.63 (ddd, J= 13.2, 7.0, 2.8 Hz, 1H), 6.53 - 6.41 (m, 2H). ESI-MS m/z calc. 279.03748, found 280.2 (M+l)+; Retention time: 0.83 minutes. Final purity was determined by reversed phase UPLC using an Acquity UPLC Acquity CSH Cl 8 (2.1 x 50 mm, 1.7 pm particle) made by Waters, and a dual gradient run from 5-95% mobile phase B over 0.6 minutes. Mobile phase A = H2O (0.1 % CF3CO2H). Mobile phase B = CH3CN (0.1 % CF3CO2H). Flow rate = 0.6 mL/min, injection volume = 2.0 pL.
53% Stage #1: 5-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine With potassium-t-butoxide; methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) dichloromethane; di-tertbutyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In <i>tert</i>-butyl alcohol at 30℃; Stage #2: 3,4-difluoro-phenylamine In <i>tert</i>-butyl alcohol at 30℃; 4.1 Weighed 5-bromo-6-chloro-lH-pyrrolo[2,3-b]pyridine (944.5 mg, 4.080 mmol), t-butyl XPhos Palladacycle generation 4 (362 mg, 0.4052 mmol), potassium t-butoxide (1.372 g, 12.23 mmol), and ditert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl] phosphane (362 mg, 0.8525 mmol) into a 40 mL vial. Added t-butanol (21 mL) and wanned in a 30 °C heating block. Degassed with Nz for 1 minute. Added 3,4-difluoroaniline (425 pL, 4.286 mmol) and stirred at 30 °C overnight. Diluted with dichloromethane (100 mL). Washed the organics with 0.5 M HC1 aqueous solution (50 mL), and washed the aqueous phase with 10% methanol in Agent Ref. 10275.0199-00304 dichloromethane (100 mL). Combined the organic phases and dried over NaiSCU, filtered, added celite and evaporated the solvent under reduced pressure. Purification by silica gel chromatography on 80 g of Silica in a gold cartridge: (Gradient: 0-100 % ethyl acetate in heptane). Concentrated the desired fractions to dryness under reduced pressure to yield the product as a white solid, 6-chloro-N-(3,4-difluorophenyl)-lH-pyrrolo[2,3-b]pyridin-5-amine (620 mg, 53%) 1H NMR (300 MHz, DMSO-d6) 8 11.82 (s, 1H), 7.95 (s, 1H), 7.84 (s, 1H), 7.55 - 7.46 (m, 1H), 7.24 - 7.11 (m, 1H), 6.63 (ddd, J= 13.2, 7.0, 2.8 Hz, 1H), 6.53 - 6.41 (m, 2H). ESI-MS m/z calc. 279.03748, found 280.2 (M+l)+; Retention time: 0.83 minutes. Final purity was determined by reversed phase UPLC using an Acquity UPLC Acquity CSH Cl 8 (2.1 x 50 mm, 1.7 pm particle) made by Waters, and a dual gradient run from 5-95% mobile phase B over 0.6 minutes. Mobile phase A = H2O (0.1 % CF3CO2H). Mobile phase B = CH3CN (0.1 % CF3CO2H). Flow rate = 0.6 mL/min, injection volume = 2.0 pL.
  • 28
  • [ 1190321-59-5 ]
  • [ 3863-11-4 ]
  • 4-[11-(2-cyano-1,1-dimethyl-ethyl)-10-(3,4-difluorophenyl)-2,4,10-triazatricyclo[7.3.0.03,7] dodeca-1,3(7),5,8,11-pentaen-12-yl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium-t-butoxide; di-tertbutyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane; tBuXPhos Pd G4 / <i>tert</i>-butyl alcohol / 30 °C 1.2: 30 °C 2.1: N-cyclohexyl-N-methylcyclohexanamine / 1,4-dioxane / 0.17 h / Inert atmosphere 2.2: 18 h / 80 °C 2.3: 2 h / 50 °C
Multi-step reaction with 2 steps 1.1: potassium-t-butoxide; di-tertbutyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane; methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) dichloromethane / <i>tert</i>-butyl alcohol / 30 °C 1.2: 30 °C 2.1: bis(tri-tertiary-butylphosphine)palladium(0); N-cyclohexyl-N-methylcyclohexanamine / 1,4-dioxane / 18 h / 80 °C 2.2: 2 h / 50 °C
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