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[ CAS No. 1245649-96-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1245649-96-0
Chemical Structure| 1245649-96-0
Chemical Structure| 1245649-96-0
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Product Details of [ 1245649-96-0 ]

CAS No. :1245649-96-0 MDL No. :MFCD14706800
Formula : C6H3BrClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :YMVUEHXTDWJMIW-UHFFFAOYSA-N
M.W : 232.47 Pubchem ID :70700431
Synonyms :

Calculated chemistry of [ 1245649-96-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.6
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 2.89
Consensus Log Po/w : 2.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.0839 mg/ml ; 0.000361 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.239 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0225 mg/ml ; 0.0000968 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 1245649-96-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1245649-96-0 ]

* 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 [ 1245649-96-0 ]

[ 1245649-96-0 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 59782-85-3 ]
  • [ 1245649-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 2 h / 0 - 30 °C 2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 20 °C 3.1: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 4.1: tert.-butylnitrite / Bromoform / 2 h / 61 - 90 °C
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 1.2: 2 h / 0 - 30 °C 2.1: triethylamine; trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 3.1: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 4.1: tert.-butylnitrite / Bromoform / 2 h / 61 - 90 °C
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 20 °C 3.1: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 4.1: Bromoform; tert.-butylnitrite / 2 h / 61 - 90 °C
  • 2
  • [ 75291-86-0 ]
  • [ 1245649-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 20 °C 2: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 3: tert.-butylnitrite / Bromoform / 2 h / 61 - 90 °C
Multi-step reaction with 3 steps 1: triethylamine; trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 2: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 3: tert.-butylnitrite / Bromoform / 2 h / 61 - 90 °C
Multi-step reaction with 3 steps 1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 20 °C 2: hydrazine hydrate / butan-1-ol / 7 h / 120 °C 3: Bromoform; tert.-butylnitrite / 2 h / 61 - 90 °C
  • 3
  • [ 126954-66-3 ]
  • 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
  • 4
  • [ 1245643-75-7 ]
  • [ 1245649-96-0 ]
YieldReaction ConditionsOperation in experiment
49% With tert.-butylnitrite In Bromoform at 61 - 90℃; for 2h; 1.10 Step 10) 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine 5-Chloro-1H-pyrazolo[3,4-b]pyridin-3-amine (694 mg, 4.12 mmol)It was dissolved in bromoform (5 mL), and then tert-butyl nitrite (1.2 mL, 10.0 mmol) was added thereto, and the mixture was reacted at 61 ° C for 1 hour.Then, the mixture was transferred to a temperature of 90 ° C for another hour. Stop the reaction,The bromine was distilled off under reduced pressure, and ethyl acetate was added to dissolve the residue.Then concentrate under reduced pressure.The residue was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 4/1)Purification to give the title compound as a yellow powder(471 mg, 49%).
49% With tert.-butylnitrite In Bromoform at 61 - 90℃; for 2h; 1.10 Step 10: 3 -bromo-5-chloro- 1H-pyrazolo[3 ,4-blpyridine To a solution of 5-chloro-1H-pyrazolo[3,4-b]pyridin-3-amine (694 mg, 4.12 mmol) in bromoform (5 mL) was added tert-butyl nitrite (1.2 mL, 10.0 mmol). The mixture was stirred at 61 °C for 1 h, then heated to 90 °C and stirred for further 1 h. The reaction was stopped, and the reaction mixture was concentrated in vacuo to remove bromoform. The residue was dissolve in ethyl acetate and then the mixture was concentrated. The resulting residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 4/1) to give the title compound as yellow powder (471 mg, 49%).MS (ESI, pos. ion) m/z: 233.9 [M+H]‘HNMR(4001V11{z,DMSO-d6)E(ppm): 14.03 (d,J206.4Hz, 1H), 8.61 (dd,J= 18.1, 1.7Hz, 1H), 8.28 (dd, J= 10.7, 2.0 Hz, 1H).
49% With tert.-butylnitrite; Bromoform at 61 - 90℃; for 2h; 6.7 Step 7) 3-Bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine 5-Chloro-1H-pyrazolo[3,4-b]pyridin-3-amine (694 mg, 4.12 mmol)SolubleIn bromoform (5mL),Then, t-butyl nitrite (1.2 mL, 10.0 mmol) was added thereto.The resulting mixture was reacted at 61 ° C for 1 hour.Then, the mixture was transferred to a temperature of 90 ° C for 1 hour.The reaction was stopped, bromine was distilled off under reduced pressure, and ethyl acetate was added to dissolve the residue.Then concentrate under reduced pressure,The residue was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 4/1)The title compound was obtained as a yellow powder (471 mg, 49%).
  • 5
  • [ 1245649-96-0 ]
  • [ 2234864-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 6
  • [ 1245649-96-0 ]
  • [ 2234864-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 7
  • [ 1245649-96-0 ]
  • [ 2234864-27-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 8
  • [ 1245649-96-0 ]
  • [ 2234864-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 9
  • [ 1245649-96-0 ]
  • [ 2234864-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 10
  • [ 1245649-96-0 ]
  • [ 2234864-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 11
  • [ 1245649-96-0 ]
  • [ 2234864-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 12
  • [ 1245649-96-0 ]
  • [ 2234864-35-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 13
  • [ 1245649-96-0 ]
  • [ 2234864-33-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
  • 14
  • [ 1245649-96-0 ]
  • [ 2234864-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 15
  • [ 1245649-96-0 ]
  • [ 2234864-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 16
  • [ 1245649-96-0 ]
  • [ 2234864-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 17
  • [ 1245649-96-0 ]
  • [ 2234864-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 18
  • [ 1245649-96-0 ]
  • [ 2234864-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 19
  • [ 1245649-96-0 ]
  • [ 2234864-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 20
  • [ 1245649-96-0 ]
  • [ 2234864-47-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 115 °C / Inert atmosphere
  • 21
  • [ 1245649-96-0 ]
  • [ 2234864-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 22
  • [ 1245649-96-0 ]
  • [ 2234864-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 23
  • [ 1245649-96-0 ]
  • [ 2234864-50-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 110 °C / Inert atmosphere
  • 24
  • [ 1245649-96-0 ]
  • [ 2234864-51-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 110 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 25
  • [ 1245649-96-0 ]
  • [ 2234864-49-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 110 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 26
  • [ 1245649-96-0 ]
  • [ 2234864-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 27
  • [ 1245649-96-0 ]
  • [ 2234864-77-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 28
  • [ 1245649-96-0 ]
  • [ 2234864-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 29
  • [ 1245649-96-0 ]
  • [ 2234864-86-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 30
  • [ 1245649-96-0 ]
  • [ 2234864-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 31
  • [ 1245649-96-0 ]
  • [ 2234864-85-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 32
  • [ 1245649-96-0 ]
  • [ 2234864-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
  • 33
  • [ 1245649-96-0 ]
  • [ 2234864-91-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 34
  • [ 1245649-96-0 ]
  • [ 2234864-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
  • 35
  • [ 1245649-96-0 ]
  • [ 2234864-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1.5 h / 115 °C / Inert atmosphere
  • 36
  • [ 1245649-96-0 ]
  • [ 2234865-11-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 37
  • [ 1245649-96-0 ]
  • [ 2234865-10-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 38
  • [ 1245649-96-0 ]
  • [ 2234865-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; XPhos; palladium diacetate / tetrahydrofuran; water / 12 h / 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; palladium diacetate; XPhos / water; tetrahydrofuran / 12 h / 80 °C
  • 39
  • [ 1245649-96-0 ]
  • [ 2234866-12-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; XPhos; palladium diacetate / tetrahydrofuran; water / 12 h / 80 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; palladium diacetate; XPhos / water; tetrahydrofuran / 12 h / 80 °C 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 40
  • [ 1245649-96-0 ]
  • [ 2234865-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 41
  • [ 1245649-96-0 ]
  • [ 2234865-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 42
  • [ 1245649-96-0 ]
  • [ 2234865-14-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; water; ethanol / 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide; water / tetrahydrofuran; ethanol / 2 h / 20 °C
  • 43
  • [ 1245649-96-0 ]
  • [ 2234865-18-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 44
  • [ 1245649-96-0 ]
  • [ 2234865-19-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 45
  • [ 1245649-96-0 ]
  • [ 2234865-17-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; water; ethanol / 2 h / 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide; water / tetrahydrofuran; ethanol / 2 h / 20 °C
  • 46
  • [ 1245649-96-0 ]
  • [ 1383446-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere
  • 47
  • [ 1245649-96-0 ]
  • [ 2234864-10-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube
  • 48
  • [ 1245649-96-0 ]
  • [ 2234864-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C
  • 49
  • [ 1245649-96-0 ]
  • [ 2234864-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 2 h / 105 °C / Inert atmosphere 3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 115 °C / Inert atmosphere; Sealed tube 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C 5.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
  • 50
  • [ 1245649-96-0 ]
  • [ 76-83-5 ]
  • [ 2234864-00-5 ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: trityl chloride at 20℃; 1.11 Step 11) 3-Bromo-5-chloro-1-trityl-1H-pyrazolo[3,4-b]pyridine 3-Bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine (471 mg, 2.03 mmol)It was dissolved in DMF (5 mL), and K2CO3 (98 mg, 6.11 mmol) was added thereto at 0 °C.And stirred at this temperature for 30 minutes.Then add triphenylchloromethane (677 mg, 2.43 mmol),The mixture was transferred to room temperature and stirring was continued overnight. The reaction was quenched by adding water (50 mL), and the mixture was separated.The aqueous phase was extracted with ethyl acetate (80 mL×2).The combined organic phases were washed with saturated brine (80 mL×3).Dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure.The residue was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a yellow solid(425 mg, 44%).
44% Stage #1: 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: trityl chloride In N,N-dimethyl-formamide at 20℃; 1.11 Step 11: 3 -bromo-5-chloro- 1 -trityl- 1H-pyrazolo[3 ,4-blpyridine To a solution of 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine (471 mg, 2.03 mmol) in DMF (5 mL) was added K2C03 (98 mg, 6.11 mmol) at 0 °C. Then the reaction mixture was stirred for 30 mm at 0 °C. Triphenylchloromethane (677 mg, 2.43 mmol) was added and the reaction mixture was stirred at rt overnight. Water (50 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (80 mL x 2). The combined organic phases were washed with saturated brine (80 mLx 3), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 4/1) to give the title compound as a yellow solid (425 mg, 44 %).‘H NMR (400 MHz, CDC13) (ppm): 8.38 (d, J 2.3 Hz, 1H), 8.26 (d, J 2.3 Hz, 1H), 7.31 - 7.19(m, 15H).
44% Stage #1: 3-bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: trityl chloride In N,N-dimethyl-formamide at 20℃; 6.8 Step 8) 3-Bromo-5-chloro-1-trityl-1H-pyrazolo[3,4-b]pyridine 3-Bromo-5-chloro-1H-pyrazolo[3,4-b]pyridine (471 mg, 2.03 mmol)Soluble in DMF (5mL),K2CO3 (98 mg, 6.11 mmol) was added thereto at 0 °C.And stirred at this temperature for 30 minutes.Then add triphenylchloromethane(677mg, 2.43mmol),The mixture was transferred to room temperature and stirring was continued overnight.The reaction was quenched by adding water (50 mL), and the mixture was separated.The aqueous phase was extracted with ethyl acetate (80 mL×2).The combined organic phases were washed with saturated brine (80 mL×3).Dry over anhydrous sodium sulfate,Filtration, the filtrate is evaporated under reduced pressure,The residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate (v/v)=4/1)The title compound was obtained as a yellow solid (425mg, 44%).
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