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[ CAS No. 1211331-43-9 ]

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Product Details of [ 1211331-43-9 ]

CAS No. :1211331-43-9 MDL No. :MFCD12827553
Formula : C5H2BrF2N Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :193.98 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1211331-43-9 ]

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

Application In Synthesis of [ 1211331-43-9 ]

* 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 [ 1211331-43-9 ]

[ 1211331-43-9 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 21717-96-4 ]
  • [ 1211331-43-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 20 °C 2: pyridine; sodium nitrite; hydrogen fluoride / 1.5 h / 0 - 50 °C / polyethylene reaction vessel
  • 2
  • [ 869557-43-7 ]
  • [ 1211331-43-9 ]
YieldReaction ConditionsOperation in experiment
68% NaN02 (1.4 g, 14.4 mmol) was added in portions to a solution of 3-bromo-5- fluoro-pyridin-2-ylamine (5.2 g, 17.3 mmol) in a HF/pyridine mixture (40 mL) in a polyethylene reaction vessel. The resulting mixture was stirred at 0 C for 0.5 h, then heated to 50 C and stirred for 1 h. The reaction mixture was poured onto crushed ice, partially neutralized with Na2C03, and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the product (4.1 g, 68%) as a white solid.
42% (8a) 3-Bromo-2,5-difluoropyridine Sodium nitrite (1.97 g, 28.6 mmol) was added in small portions to a solution of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (WO20062578 A1, 3.64 g, 19.1 mmol) in hydrofluoric acid pyridine (10 mL) at -10C. After stirring at room temperature for two hours, water (100 mL) and sodium bicarbonate were added to the reaction mixture at 0C, followed by extraction with ethyl acetate (100 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride) to obtain the title compound (1.56 g, 42%) as a brown liquid. 1H-NMR (400 MHz, CDCl3): delta ppm: 7.78 (1H, dt, J = 2.7, 6.7 Hz), 8.02 (1H, dd, J = 1.6, 2.4 Hz).
42% With pyridine hydrogenfluoride; sodium nitrite; at -10 - 20℃; for 2h; Sodium nitrite (1.97 g, 28.6 mmol) was added in small portions to a solution of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (, 3.64 g, 19.1 mmol) in hydrogen fluoride-pyridine (10 mL) at -10C. After stirring at room temperature for two hours, water (100 mL) and sodium bicarbonate were added to the reaction mixture at 0C, followed by extraction with ethyl acetate (100 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride) to obtain the title compound (1.56 g, 42%) as a brown liquid. 1H-NMR (400 MHz, CDCl3): delta ppm: 7.78 (1H, dt, J = 2.7, 6.7 Hz), 8.02 (1H, dd, J = 1.6, 2.4 Hz).
With pyridine hydrogenfluoride; sodium nitrite; at 10 - 20℃; for 2h; To a mixture of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (1.50 g, 7.85 mmol) and hydrogen fluoride pyridine (4 mL, 44 mmol), sodium nitrite (0.813 g, 11.8 mmol) was added at -10C in a several portions, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate until it became basic, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of 3-bromo- 2, 5-difluoropyridine .
With pyridine hydrofluoride; sodium nitrite; at -10 - 20℃; for 2h; To a mixture of 3-bromo-5-fluoro-pyridin-2-amine(1.50 g, 7.85 mmol) and hydrogen fluoride pyridine (4 mL, 44 mmol), sodium nitrite was added at -10C in a several portions, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted by addition of asaturated aqueous solution of sodium bicarbonate until it became basic, followed by extraction with ethyl acetate.The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of 3-bromo-2,5-difluoro-pyridine (1.00 g) . To a solution of a crude product of 3-bromo-2,5-difluoro- pyridine (1.00 g) obtained in the above step in ethanol (20 mL), a 20% ethanol solution of sodium ethoxide (2.84 mL, 6.61 mmol) was added at room temperature, andthe mixture was stirred at 80C for 1 hour in an oil bath.The mixture was cooled, and concentrated under reducedpressure. The residue was purified in an automaticchromatography apparatus (n-hexane/ethyl acetate = 100/0- 90/10) to obtain the title compound (1.04 g, yield for2 steps: 66%)?H NNR spectrum (CDC13, 400MHz) oe: 8.02 (1H, d, J =2.3 Hz), 7.80 (1H, d, J= 2.3 Hz), 4.41 (2H, q, J=7.0 Hz), 1.43 (3H, t, J = 7.0 Hz)
With pyridine hydrofluoride; sodium nitrite; at -10 - 60℃; for 1.5h; 3-Bromo-5-fluoro-pyridin-2-ylamine (2.17 g, 11.361 mmol) was taken in pyridine hydrogen fluoride (15 mL) and cooled at -10 C. Sodium nitrite (1.176 g, 17.042 mmol) was added portionwise over 30 minutes. The mixture was allowed to come to room temperature and finally heated at 60 C. for 1 h. The mixture was poured onto crushed ice (ca 50 g). The mixture was neutralized with 1M Na2CO3 and organics extracted with EA (2*100 mL). The organic layers were further washed with brine, dried over MgSO4, filtered and concentrated to the crude 3-bromo-2,5-difluoro-pyridine as a brownish oil (1.48 g, 66%).

  • 3
  • [ 1211331-43-9 ]
  • [ 287944-16-5 ]
  • [ 1349185-09-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,4-dioxane; water Reflux; Inert atmosphere; 4.3 To a solution of 3-bromo-2, 5-dif uoro-pyridine (4.1 g, 20.8 mmol) in dioxane (60 mL) was treated with Na2C03 (4.4 g, 41.6 mmol) in 20 mL of H20 as a solution, followed by additional of 4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (4.8 g 22.9 mmol) and Pd(dppf)Cl2 (761 mg). The resulting mixture was heated at refluxing overnight under N2 atmosphere. TLC showed that most of the staring materials were consumed. The solution was filtered and the filtrate was concentrated to get a residue, which was purified by silica gel chromatography to give the product (3.7 g).
  • 4
  • [ 1211331-43-9 ]
  • [ 1349184-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / dimethyl sulfoxide / 80 °C 2: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 110 °C / Inert atmosphere
  • 5
  • [ 1211331-43-9 ]
  • [ 1349184-84-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / dimethyl sulfoxide / 80 °C 2: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 110 °C / Inert atmosphere 3: hydrogen / palladium on activated charcoal / methanol / 30 °C / 2068.65 Torr
  • 6
  • [ 1211331-43-9 ]
  • [ 1349184-85-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 80 °C 2: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 110 °C / Inert atmosphere 3: hydrogen / palladium on activated charcoal / methanol / 30 °C / 2068.65 Torr 4: hydrogenchloride / methanol / 2 h / 20 °C
  • 7
  • [ 1211331-43-9 ]
  • [ 1349185-10-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2: hydrogen / palladium on activated charcoal / methanol / 20 °C
  • 8
  • [ 1211331-43-9 ]
  • [ 1349185-11-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 3.2: 3 h / 60 °C
  • 9
  • [ 1211331-43-9 ]
  • [ 1349185-12-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 3.2: 3 h / 60 °C 4.1: lithium hydroxide / water; methanol / 1 h / 20 - 50 °C
  • 10
  • [ 1211331-43-9 ]
  • [ 1349185-13-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 3.2: 3 h / 60 °C 4.1: lithium hydroxide / water; methanol / 1 h / 20 - 50 °C 5.1: triethylamine; HATU / N,N-dimethyl-formamide / 24 h / 20 °C
  • 11
  • [ 1211331-43-9 ]
  • [ 1349185-14-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 3.2: 3 h / 60 °C 4.1: lithium hydroxide / water; methanol / 1 h / 20 - 50 °C 5.1: triethylamine; HATU / N,N-dimethyl-formamide / 24 h / 20 °C 6.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 6.2: 0.5 h / -78 °C 6.3: 20 °C
  • 12
  • [ 1211331-43-9 ]
  • cis-(1H-benzoimidazol-2-yl)-{3-[5-fluoro-3-(tetrahydropyran-4-yl)-pyridin-2-yloxy]cyclobutyl}methanone [ No CAS ]
  • trans-(1H-benzoimidazol-2-yl)-{3-[5-fluoro-3-(tetrahydropyran-4-yl)pyridin-2-yloxy]cyclobutyl}methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 3.2: 3 h / 60 °C 4.1: lithium hydroxide / water; methanol / 1 h / 20 - 50 °C 5.1: triethylamine; HATU / N,N-dimethyl-formamide / 24 h / 20 °C 6.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 6.2: 0.5 h / -78 °C 6.3: 20 °C 7.1: hydrogenchloride / tetrahydrofuran / 7 h / 20 - 60 °C
  • 13
  • [ 1211331-43-9 ]
  • cis-benzothiazol-2-yl-{3-[5-fluoro-3-(tetrahydropyran-4-yl)-pyridin-2-yl]cyclobutyl}amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 2 h / 100 °C / Inert atmosphere
  • 14
  • [ 1211331-43-9 ]
  • trans-benzothiazol-2-yl-{3-[5-fluoro-3-(tetrahydropyran-4-yl)pyridin-2-yl]cyclobutyl}amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Reflux; Inert atmosphere 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 2 h / 100 °C / Inert atmosphere
  • 15
  • [ 389890-43-1 ]
  • [ 1211331-43-9 ]
  • [ 1349184-78-6 ]
YieldReaction ConditionsOperation in experiment
41% With caesium carbonate; In dimethyl sulfoxide; at 80℃; To a mixture of 3-bromo-2,5-difluoro-pyridine (500 mg, 2.58 mmol ) and tert- butyl ((l S,3S)-3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 485 mg, 2.58 mmol) in DMSO (20 mL) was added CS2CO3 (1.68 g, 5.16 mmol), and then the mixture was stirred at 80C overnight. The reaction mixture was diluted with water and extracted with EtOAc (3 x 50 mL), washed with brine and dried over Na2S04. The dried organic layers were concentrated to tert-butyl ((l S,3S)-3-((3-bromo-5-fluoropyridin-2-yl)oxy)cyclobutyl)carbamate (380 mg, 1.06 mmol, 41%). ESI-MS (M+l): 361 calc. for Ci4H18BrFN203 360.
  • 16
  • [ 1211331-43-9 ]
  • 2-ethoxy-5-fluoropyridine-3-sulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 97 h / 20 - 80 °C 2: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere 3: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / acetonitrile; water / 3 h / Cooling with ice
Multi-step reaction with 3 steps 1: ethanol / 1 h / 20 - 80 °C 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere 3: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / water; acetonitrile / 3 h / 20 °C / Cooling with ice
  • 17
  • [ 1211331-43-9 ]
  • 3-(benzylsulfanyl)-2-ethoxy-5-fluoropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 97 h / 20 - 80 °C 2: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: ethanol / 1 h / 20 - 80 °C 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere
  • 18
  • [ 1211331-43-9 ]
  • 2-methoxyethyl (3R)-7-[(2-ethoxy-5-fluoropyridin-3-yl)sulfonyl]amino}-3-methyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethanol / 97 h / 20 - 80 °C 2.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / acetonitrile; water / 3 h / Cooling with ice 4.1: hydrogenchloride / 1,4-dioxane; methanol / 0.83 h / 20 °C 4.2: 0.67 h / 80 °C
  • 19
  • [ 1211331-43-9 ]
  • potassium [(2-ethoxy-5-fluoropyridin-3-yl)sulfonyl]{(3R)-4-[(2-methoxyethoxy)carbonyl]-3-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-7-yl}azanide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethanol / 97 h / 20 - 80 °C 2.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / acetonitrile; water / 3 h / Cooling with ice 4.1: hydrogenchloride / 1,4-dioxane; methanol / 0.83 h / 20 °C 4.2: 0.67 h / 80 °C 5.1: potassium hydroxide / ethanol / 2 h / 20 °C
  • 20
  • [ 1211331-43-9 ]
  • [ 141-52-6 ]
  • 3-bromo-2-ethoxy-5-fluoropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
811 mg In ethanol at 20 - 80℃; for 97h; 38.38a (38a) 3-bromo-2-ethoxy-5-fluoropyridine To a solution of a crude product of 3-bromo-2 , 5-difluoropyridine obtained in the above step in ethanol (40 mL) , a 20% ethanol solution of sodium ethoxide (5.04 mL, 11.8 mmol) was added at room (1188) temperature, the mixture was stirred at the same (1189) temperature as above for 4 days, and subsequently stirred at 80°C for 1 hour in an oil bath. The mixture was cooled, and concentrated under reduced pressure. The residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0 - 90/10) to obtain the title compound (811 mg, yield for (1190) 2 steps : 47%) . NMR spectrum (CDCI3, 400MHz) δ: 7.95 (1H, d, J = (1191) 2.7 Hz), 7.63 (1H, dd, J = 7.0, 2.7 Hz), 4.39 (2H, q, J = (1192) 7.0 Hz), 1.42 (3H, t, J = 7.0 Hz) .
1.04 g In ethanol at 20 - 80℃; for 1h; 14.14a (14a) 3-bromo-2-ethoxy-5-fluoropyridine To a mixture of 3-bromo-5-fluoro-pyridin-2-amine(1.50 g, 7.85 mmol) and hydrogen fluoride pyridine (4 mL, 44 mmol), sodium nitrite was added at -10°C in a several portions, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted by addition of asaturated aqueous solution of sodium bicarbonate until it became basic, followed by extraction with ethyl acetate.The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of 3-bromo-2,5-difluoro-pyridine (1.00 g) . To a solution of a crude product of 3-bromo-2,5-difluoro- pyridine (1.00 g) obtained in the above step in ethanol (20 mL), a 20% ethanol solution of sodium ethoxide (2.84 mL, 6.61 mmol) was added at room temperature, andthe mixture was stirred at 80°C for 1 hour in an oil bath.The mixture was cooled, and concentrated under reducedpressure. The residue was purified in an automaticchromatography apparatus (n-hexane/ethyl acetate = 100/0- 90/10) to obtain the title compound (1.04 g, yield for2 steps: 66%)‘H NNR spectrum (CDC13, 400MHz) ö: 8.02 (1H, d, J =2.3 Hz), 7.80 (1H, d, J= 2.3 Hz), 4.41 (2H, q, J=7.0 Hz), 1.43 (3H, t, J = 7.0 Hz)
  • 21
  • [ 1211331-43-9 ]
  • 2-ethoxy-5-fluoro-N-[(5S)-5-methyl-5,6-dihydropyrazolo[1,5-d]pyrido[3,2-f][1,4]oxazepin-10-yl]pyridine-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethanol / 1 h / 20 - 80 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / water; acetonitrile / 3 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / methanol; 1,4-dioxane / 3 h / 20 °C 4.2: 0.5 h / 20 - 80 °C
  • 22
  • [ 1211331-43-9 ]
  • potassium [(2-ethoxy-5-fluoropyridin-3-yl)sulfonyl][(5S)-5-methyl-5,6-dihydropyrazolo[1,5-d]pyrido[3,2-f][1,4]oxazepin-10-yl]azanide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethanol / 1 h / 20 - 80 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / water; acetonitrile / 3 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / methanol; 1,4-dioxane / 3 h / 20 °C 4.2: 0.5 h / 20 - 80 °C 5.1: potassium hydroxide / ethanol / 2 h / 20 °C
  • 23
  • [ 1211331-43-9 ]
  • N-(5,6-dihydropyrazolo[1,5-d]pyrido[3,2-f][1,4]oxazepin-10-yl)-2-ethoxy-5-fluoropyridine-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethanol / 1 h / 20 - 80 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / water; acetonitrile / 3 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / methanol; 1,4-dioxane / 4 h / 20 °C 4.2: 2 h / 20 - 80 °C
  • 24
  • [ 1211331-43-9 ]
  • potassium 5,6-dihydropyrazolo[1,5-d]pyrido[3,2-f][1,4]oxazepin-10-yl[(2-ethoxy-5-fluoropyridin-3-yl)sulfonyl]azanide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethanol / 1 h / 20 - 80 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 20 - 100 °C / Inert atmosphere 3.1: 1,3-dichloro-5,5-dimethylhydantoin; acetic acid / water; acetonitrile / 3 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / methanol; 1,4-dioxane / 4 h / 20 °C 4.2: 2 h / 20 - 80 °C 5.1: potassium hydroxide / ethanol / 1 h / 20 °C
  • 25
  • [ 1211331-43-9 ]
  • [ 1242328-95-5 ]
  • [ 1242329-12-9 ]
YieldReaction ConditionsOperation in experiment
54% With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; 67 4.8 General procedure for Copper-catalyzed coupling reaction to prepare 14 (General procedure G) General procedure: A solution of 13 (3.12g, 10.0mmol), 2-fluoro or 2-bromo substituted pyridine (11.0mmol), CuI (0.19g, 1.00mmol), 1,10-phenanthroline (0.18g, 1.00mmol) and Cs2CO3 (9.77g, 30mmol) in DMF (50mL) was stirred under N2 at 80°C for 2h. Aqueous NH4Cl solution (10%) was added to the cooled reaction mixture, and the mixture was extracted with EtOAc several times. The combined organic layers were washed with water and dried over anhydrous Na2SO4. After concentration under reduced pressure, the residue was purified by silica gel chromatography to obtain 14.
  • 26
  • [ 1211331-43-9 ]
  • 4-[(1R)-1-aminoethyl]cyclohexanol hydrochloride [ No CAS ]
  • 4-[(1R)-1-[(3-bromo-5-fluoro-2-pyridyl)amino]ethyl]cyclohexanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.96% Stage #1: 4-[(1R)-1-aminoethyl]cyclohexanol hydrochloride With potassium carbonate In N,N-dimethyl-formamide at 15℃; for 0.5h; Stage #2: 3-bromo-2,5-difluoro-pyridine In N,N-dimethyl-formamide at 120℃; for 8h; 28.1 Step 1: 4-[(lR)-l-[(3-Bromo-5-fluoro-2-pyridyl)amino]ethyl]cyclohexanol To a solution of 4-[(lR)- l-aminoethyl]cyclohexanol hydrochloride (5.6 g, 30.9 mmol, 1.2 eq) in DMF (25 mL) was added K2CO3 (10.7 g, 77.3 mmol, 3 eq). The mixture was stirred at 15°C for 0.5h. 3-Bromo-2,5-difluoro-pyridine (5 g, 25.8 mmol, 1 eq) was added and the mixture was stirred at 120°C for 8h. LCMS detected desired compound. The reaction mixture was concentrated to dryness, H20 (lOOmL) was added, and extracted with ethyl acetate (180mL x 3). The combined organic layer was washed with brine (80mL), dried over Na2S04, filtered and concentrated. The residue was purified by flash silica gel chromatography (ISCO; 80 g SepaFlash Silica Flash Column, eluent of 0-45% ethyl acetate/Petroleum ether gradient 60 mL/min). 4-[(lR)- l-[(3-Bromo-5-fluoro-2- pyridyl)amino]ethyl]cyclohexanol (5.2 g, 16.23 mmol, 62.96% yield, 99% purity) was obtained as yellow oil. LCMS (M+H+) m/z: calcd 317.06; found 317.1.
  • 27
  • [ 1211331-43-9 ]
  • 1-((R)-1-(4-(3-cyclopropoxyazetidin-1-yl)cyclohexyl)ethyl)-5-fluoro-2-methyl-N-((6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C 5.1: sodium hydroxide; water / 12 h / 80 °C 6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 30 °C 6.2: 12 h / 30 °C
  • 28
  • [ 1211331-43-9 ]
  • 1-((R)-1-(4-(3-cyclopropoxyazetidin-1-yl)cyclohexyl)ethyl)-5-fluoro-2-methyl-N-((6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C 5.1: sodium hydroxide; water / ethanol / 12 h / 80 °C 6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 30 °C 6.2: 12 h / 30 °C
  • 29
  • [ 1211331-43-9 ]
  • ethyl 5-fluoro-1-[(1R)-1-(4-hydroxycyclohexyl)ethyl]-2-methylpyrrolo[2,3-b]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation
  • 30
  • [ 1211331-43-9 ]
  • ethyl 5-fluoro-2-methyl-1-[(1R)-1-(4-oxocyclohexyl)ethyl]pyrrolo[2,3-b]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C
  • 31
  • [ 1211331-43-9 ]
  • ethyl 1-[(1R)-1-[4-[3-(cyclopropoxy)azetidin-1-yl]cyclohexyl]ethyl]-5-fluoro-2-methylpyrrolo[2,3-b]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C
  • 32
  • [ 1211331-43-9 ]
  • ethyl 1-[(1R)-1-[4-[3-(cyclopropoxy)azetidin-1-yl]cyclohexyl]ethyl]-5-fluoro-2-methylpyrrolo[2,3-b]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C
  • 33
  • [ 1211331-43-9 ]
  • 1-[(1R)-1-[4-[3-(cyclopropoxy)azetidin-1-yl]cyclohexyl]ethyl]-5-fluoro-2-methylpyrrolo[2,3-b]pyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C 5.1: sodium hydroxide; water / 12 h / 80 °C
  • 34
  • [ 1211331-43-9 ]
  • 1-[(1R)-1-[4-[3-(cyclopropoxy)azetidin-1-yl]cyclohexyl]ethyl]-5-fluoro-2-methylpyrrolo[2,3-b]pyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 15 °C 1.2: 8 h / 120 °C 2.1: copper(l) iodide; potassium iodide; caesium carbonate; 2-Picolinic acid / N,N-dimethyl-formamide / 150 °C / Sealed tube; Microwave irradiation 3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 15 °C 4.1: N-ethyl-N,N-diisopropylamine / methanol / 1 h / 15 °C 4.2: 1.5 h / 15 °C 4.3: 0.5 h / -70 °C 5.1: sodium hydroxide; water / ethanol / 12 h / 80 °C
  • 35
  • [ 1211331-43-9 ]
  • 1-(3-bromo-5-fluoropyridin-2-yl)-N-(5-cyano-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrazine hydrate / ethanol / 80 °C 2: triethylamine / ethanol / 80 °C 3: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.75 h / 20 °C / Reflux 5: triethylamine / tetrahydrofuran; dichloromethane / 20 °C
  • 36
  • [ 1211331-43-9 ]
  • (3-bromo-5-fluoropyridin-2-yl)hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.36 g With hydrazine hydrate In ethanol at 80℃; 34.B B.
(3-Bromo-5-fluoro-pyridin-2-yl)-hydrazine, cpd 34b
Hydrazine monohydrate (1.95 mL, 25.518 mmol) was added to a solution of 3-bromo-2,5-difluoro-pyridine, cpd 34a (1.65 g, 8.506 mmol) in ethanol (15 mL) and stirred at 80° C. overnight. The mixture was then allowed to cool to room temperature and partially concentrated till the desired product crystallized. Water was added and suspension stirred for 30 minutes. The precipitate was filtered and washed with water. Air drying afforded the pure hydrazine (1.36 g, 72%). 1H NMR (300 MHz, DMSO-d6) δ 4.18 (s, 2H), 7.36 (s, 1H), 7.93 (dd, J=7.8, 2.5 Hz, 1H), 8.14 (d, J=2.6 Hz, 1H). MS m/z 206 (MH+).
  • 37
  • [ 1211331-43-9 ]
  • ethyl 1-(3-bromo-5-fluoropyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 80 °C 2: triethylamine / ethanol / 80 °C
  • 38
  • [ 1211331-43-9 ]
  • 1-(3-bromo-5-fluoropyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / 80 °C 2: triethylamine / ethanol / 80 °C 3: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C
  • 39
  • [ 1211331-43-9 ]
  • C10H3BrClF4N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 80 °C 2: triethylamine / ethanol / 80 °C 3: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.75 h / 20 °C / Reflux
  • 40
  • [ 1211331-43-9 ]
  • 1-(3-cyano-5-fluoropyridin-2-yl)-N-(5-cyano-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrazine hydrate / ethanol / 80 °C 2: triethylamine / ethanol / 80 °C 3: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 4: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.75 h / 20 °C / Reflux 5: triethylamine / tetrahydrofuran; dichloromethane / 20 °C 6: copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / Inert atmosphere
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