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CAS No. : | 865869-26-7 | MDL No. : | MFCD11520541 |
Formula : | C13H23BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SVHPQFUXPUDKLE-UHFFFAOYSA-N |
M.W : | 222.13 | Pubchem ID : | 58924635 |
Synonyms : |
|
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate In DMF (N,N-dimethyl-formamide) at 80℃; for 24h; | 116 Intermediate 116 4,4, 5, 5-Tetramethyl-2- (4-methyl-1-cyclohexen-1-yl)-1, 3, 2-dioxaborolane [1,1'-Bis (diphenylphosphino) ferrocene] dichloropalladium (II) (167 mg, 0.20 mmol) was added to a solution of Intermediate 112 (1 g, 4.09 mmol) and bis (pinacolato) diboron (3.11 g, 12.27 mmol) and potassium acetate (1.8 g, 18.4 mmol) in dry DMF (5 mL). The reaction was stirred at 80°C, under nitrogen, for 24 hours. The reaction was cooled, solvent removed, partitioned between diethyl ether and water, organics washed twice further with water, dried over sodium sulphate and concentrated. Purified by 50 g silica SPE, loaded in DCM, eluted with a gradient of DCM in cyclohexane to give the title compound which was used without further purification. Thin layer chromatography (silica) 1: 9 ethyl acetate: cyclohexane Rf = 0.8 | |
With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; Sealed tube; | 107A.2 A mixture of vinyltriflate 107a1 (6500 mg, 2.7 mmol), bis(pinacolato)diboron (770 mg, 3.1 mmol), KOAc (780 mg, 8.0 mmol), PdCI2(dppf) (97 mg, 0.13 mmol) and dppf (74 mg, 0.13 mmol) in dioxane (2 mL) is purged with Ar. The vessel is sealed then heated to 80 °C and stirred overnight. The mixture is concentrated and the residue is directly loaded onto a combiflash (eluting with 0 to 100% Et20 in Hex) to isolate vinylboronate 107a2. | |
With potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere; | 1 [206] To a stirred solution of 001B (2.20 g, 9 mmol) in dioxane (38 mL) was added bis(pinacolato)diboron (2.74 g, 10.8 mmol), [l,l'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2; 0.197 g, 0.27 mmol), l,l'-bis(diphenylphosphino)ferrocene (0.150 g, 0.27 mmol), and AcOK (potassium acetate; 2.64 g, 27 mmol). The mixture was degassed by evacuating the reaction flask under vacuum followed by N2 back-fill (3x). Under N2, the reaction was then heated to 90 °C and stirred overnight (approx. 16 hr). The reaction was cooled to room temperature (RT) and diluted with H20. The mixture was extracted with ethyl acetate (EtOAc) (3x). The combined organic layers were washed with brine, dried over MgS04, filtered, and then purified by silica gel chromatography to give compound OOIC as a clear oil. MS calcd: (M+H)+: 209. MS found: (M+H)+ = 209. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - 0 °C 1.2: -78 - 20 °C 2.1: anhydrous potassium acetate / 1,1'-bis(diphenylphosphanyl)ferrocene; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 2 steps 1.1: 2-chloropyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: Chromium (III) chloride; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium / tetrahydrofuran / 18 h / 40 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 8 h / -78 °C / Inert atmosphere 2: potassium acetate / 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 20 °C / Cooling with ice 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C 9.2: pH 4 - 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: benzyl bromide / acetonitrile / 3 h / 80 °C 3.2: 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 4 h / 20 °C 8.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 2 h / 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: acetonitrile / 3 h / 80 °C 3.1: sodium tetrahydroborate / methanol / 20 - 80 °C 4.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 4.2: 1.5 h / -77 - -70 °C / Inert atmosphere 5.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 6.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: acetonitrile / 3 h / 80 °C 3: sodium tetrahydroborate / methanol / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: acetonitrile / 3 h / 80 °C 3.1: sodium tetrahydroborate / methanol / 20 - 80 °C 4.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 4.2: 1.5 h / -77 - -70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: acetonitrile / 3 h / 80 °C 3.1: sodium tetrahydroborate / methanol / 20 - 80 °C 4.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 4.2: 1.5 h / -77 - -70 °C / Inert atmosphere 5.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: benzyl bromide / acetonitrile / 3 h / 80 °C 3.2: 80 °C 4.1: triethylamine / dichloromethane / 20 °C 4.2: 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 12 h / 80 °C 3.2: 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: benzyl bromide / acetonitrile / 3 h / 80 °C 3.2: 80 °C 4.1: triethylamine; sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: benzyl bromide / acetonitrile / 3 h / 80 °C 3.2: 80 °C 4.1: triethylamine; isobutyl chloroformate / dichloromethane / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: benzyl bromide / acetonitrile / 3 h / 80 °C 3.2: 80 °C 4.1: triethylamine; sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 8.2: 1 h / 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C 10.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 10 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C 4: sodium tetrahydroborate / methanol / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 8.2: 1 h / 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C 10.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C 7.1: dmap; HATU / N,N-dimethyl-formamide / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 3 h / 88 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C 4: sodium tetrahydroborate / methanol / 20 - 80 °C 5: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 8.1: triethylamine; sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 8.1: triethylamine; sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 80 °C / Inert atmosphere 7.1: triethylamine; benzyltrimethylammonium chloride; potassium fluoride; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 80 °C / Inert atmosphere 7.1: triethylamine; benzyltrimethylammonium chloride; potassium fluoride; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C / Inert atmosphere 8.1: sodium hydroxide / tetrahydrofuran; methanol / 20 °C 8.2: pH 5 - 6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C 4: sodium tetrahydroborate / methanol / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; carbonochloridic acid 1-chloro-ethyl ester / 1,1-dichloroethane / 20 h / Inert atmosphere 6.2: 1 h / Reflux 7.1: triethylamine; sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 20 °C 8.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 80 °C / Inert atmosphere 7.1: potassium phosphate; copper(l) iodide; trans-N,N'-dimethyl-1,2-cyclohexyldiamine / toluene / 48 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: acetonitrile / 3 h / 80 °C 3.1: sodium tetrahydroborate / methanol / 20 - 80 °C 4.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 4.2: 1.5 h / -77 - -70 °C / Inert atmosphere 5.1: triethylamine; benzyltrimethylammonium chloride; potassium fluoride; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 7.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 8.2: 1 h / 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C 8.2: 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C 7.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3: acetonitrile / 3 h / 80 °C 4: sodium tetrahydroborate / methanol / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 7.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: lithium hydroxide / ethanol; tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 0.83 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 0.83 h / 0 - 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 7.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 0.83 h / 0 - 20 °C 9.1: lithium hydroxide / ethanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr 3.1: acetonitrile / 3 h / 80 °C 4.1: sodium tetrahydroborate / methanol / 20 - 80 °C 5.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 2.5 h / -77 - -70 °C / Inert atmosphere 5.2: 1.5 h / -77 - -70 °C / Inert atmosphere 6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 4 h / 92 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine / dichloromethane / 0.83 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In water; N,N-dimethyl-formamide at 88℃; for 3h; Inert atmosphere; | 1 209] DMF (10 mL) and H20 (2 mL) were added to a mixture of OOIC (0.31 g, 1.4 mmol), 001F (0.340 g, 0.91 mmol), Pd(dppf)Cl2 (0.033 g, 0.0455 mmol), and sodium carbonate (0. 3 g, 2.8 mmol) under N2 and stirred at 88 °C for 3 hr. The reaction was cooled to RT, and to it was added ice -water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered over Celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) eluting with 0-5% MeOH in CH2C12 to give compound 001G as a solid. MS calcd:(M+H)+ = 390. MS found: (M+H)+ = 390. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In water; N,N-dimethyl-formamide at 92℃; for 4h; Inert atmosphere; | 2 [218] DMF (10 mL) and H20 (2 mL) were added to a mixture of 4-methyl-cyclohexenyl-boronic ester (0.31 g, 1.4 mmol), 002B (0.27 g, 0.91 mmol), Pd(dppf)Cl2 (0.033 g, 0.0455 mmol), and sodium carbonate (0. 3 g, 2.8 mmol) under N2, and the mixture was stirred at 92 °C for 4 hr. The reaction was cooled to RT, and to it was added ice-water and EtOAc. The organic layer was washed with water (3x) and the combined aqueous layers were back-extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure. The product was purified by flash chromatography (silica gel), eluting with 0-5% MeOH inCH2C12 to give 002C as a solid. MS calcd: (M+H)+ = 314. MS found: (M+H)+ = 314. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium periodate; ammonium acetate In water; acetone for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium periodate; ammonium acetate / water; acetone / 48 h 2: pyridine; copper diacetate; sodium sulfate / 1,2-dichloro-ethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium periodate; ammonium acetate / water; acetone / 48 h 2: pyridine; copper diacetate; sodium sulfate / 1,2-dichloro-ethane / 12 h / 25 °C 3: benzene-d6 / 10 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; | 1 Step 1: (RIS) tert-butyl 2-(methyl((3-(4-methylcyclohex-1-enyl)- 1-(tetrahydro-2H- pyran-2-yl)- 1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate [00289] A mixture of (R/S) tert-butyl N- [2-( [ [3-iodo- 1 -(oxan-2-yl)- 1 H-pyrazol-4- yl]methyl] (methyl)amino)ethyl]carbamate (50 mg, 0.11 mmol, 1.00 equiv), potassium carbonate (45 mg, 0.33 mmol, 3.02 equiv), 4,4,5 ,5-tetramethyl-2- (4-methylcyclohex- 1-en-i - yl)-1,3,2-dioxaborolane (36 mg, 0.16 mmol, 1.51 equiv), Pd(dppf)C12 (8 mg, 0.01 mmol, 0.10 equiv) in water (1 mL) and 1,4-dioxane (10 mL) was stirred under nitrogen at 100°C overnight. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 30 mg (64%) of (R/S) tert-butyl 2-(methyl((3-(4-methylcyclohex- 1 -enyl)- 1- (tetrahydro-2H-pyran-2-yl)- 1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate as a brown oil. ‘H-NMR (300 MHz, CDC13): ö 7.29 (s, 1H), 6.14-6.13 (m, 1H), 5.36-5.32 (m, 1H), 4.16-4.07 (m, 2H), 3.70-3.27 (m, 2H), 2.54-2.29 (m, 6H), 2.54-2.29 (m, 4H), 2.22 (s, 3H), 2.13-2.07 (m, 3H), 1.86-1.56 (m, 4H), 1.47 (s, 9H), 1.46-1.38 (m, 3H) ppm. LCMS (method A, ESI): RT = 1.31 mi mlz = 433.0 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 95℃; for 16h;Sealed tube; Inert atmosphere; | 4-bromo-6- chloropyridazin-3 -amine (0.3688 g, 1.7692 mmol), 4,4,5,5-tetramethyl-2-(4-methylcyclohex- 1- en-i -yl)- 1,3 ,2-dioxaborolane (393 mg, 1.7692 rnmol) (prepared from 4-methyl cyclohexanone using procedures found in patents WO 2005092863 and 2011032277), and potassium phosphate (0.7511 g, 3.5384 mmol) were placed in a sealable tube. The reaction vessel?s atmosphere waspurged with nitrogen. Dioxane (2 mL) and water (0.7 ml) added. The reaction mixture was degassed with a stream of nitrogen. Tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.173 mmol) was added. The reaction mixture was stirred at 95 C for 16 h. After cooling down, the organic supernatant was isolated, deposited on silica and purified by silica gel chromatography (eluting with ethyl acetate methanol). Concentration in vacuo of the pure fractions afforded 6-chloro-4-(4-methylcyclohex- 1-en-i -yl)pyridazin-3-amine (0.264 g, 1.1801 mmol, 67% yield). LCMS MZ (M+H) 224. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In tetrahydrofuran at 90℃; for 16h; Sealed tube; | methyl 4-bromo-1-(5-(isopropylthio)-4-(4-methylcvclohex-1-en-1-yl)thiazol-2-yl)-3-methyl-1 H- pyrazole-5-carboxylate In a 5 mL glass microwave vial equipped with a magnetic stirring bar and nitrogen flow at room temperature was placed methyl 4-bromo-1-(4-bromo-5-(isopropylthio)thiazol-2- yl)-3-methyl-1 H-pyrazole-5-carboxylate prepared as described above with respect to Compound 1 (100 mg, 0.220 mmol), 4,4,5,5-tetramethyl-2-(4-methylcyclohex-1-en-1-yl)- 1 ,3,2-dioxaborolane (41.5 mg, 0.187 mmol) and K2C03(152 mg, 1.10 mmol),nitrogen and vacuum cycles were performed (2x). Nitrogen gas was bubbled through a solution of THF (2 ml_) and then the solution was added to the microwave vial, followed by the addition of the catalyst Pd(dtbpf)CI2(14.3 mg, 0.022 mmol). The vial was capped and placed in an oil bath at 90 °C for 16 h. The solvent was evaporated under vacuum and the crude product was purified by flash chromatography on silica gel (dry packing) using a solution of EtOAc in hexanes (0 to 10% gradient) and afforded the title compound (45.6 mg, 0.097 mmol, 44%) as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine In toluene at 50℃; for 5h; Inert atmosphere; | 8 8. Synthesis of 4-methylcyclohexene-1-boronic acid pinacol ester Under nitrogen protection conditions,To a three-necked flask was added 1-bromo-4-methyl-1-cyclohexene (15 g, 85.7 mmol), boranoic acid pinacol ester (23.9 g, 94.2 mmol).Triphenylphosphine (6 mol%), trans-bis(triphenylphosphine)palladium dichloride (II)(3 mol%), potassium phenol (20.0 g, 128.5 mol)And anhydrous toluene (200 mL).After nitrogen substitution, the reaction was stirred at 50 ° C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation4-methylcyclohexene-1-boronic acid pinacol ester (15.6 g, yield: 82%). |
82% | With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine In toluene at 50℃; for 5h; Inert atmosphere; | 7 7.Synthesis of 4-methylcyclohexene-1-boronic acid pinacol ester Under nitrogen protection conditions,Add 1-bromo-4-methyl-1-cyclohexene to a three-necked vial(15g, 85.7mmol),With boronic pinacol ester (23.9g, 94.2mmol),Triphenylphosphine (6 mol%),Trans-bis(triphenylphosphine)palladium(II) chloride (3 mol%), potassium phenate (20.0 g, 128.5 mol) and anhydrous toluene (200 mL). After nitrogen substitution, the reaction was stirred at 50 ° C for 5 hours, then the system was cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine. The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure.Purification by silica gel column or distillation gave 4-methylcyclohexene-1-boronic acid pinacol ester (15.6 g, yield: 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: sodium t-butanolate / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: sodium t-butanolate / 12 h / 80 °C 3: 2-ethoxy-ethanol; water / 24 h / Reflux |
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