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[ CAS No. 1258833-77-0 ] {[proInfo.proName]}

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Product Details of [ 1258833-77-0 ]

CAS No. :1258833-77-0 MDL No. :MFCD28125257
Formula : C9H5BrFN Boiling Point : -
Linear Structure Formula :- InChI Key :ULCYLVITTXFZCK-UHFFFAOYSA-N
M.W : 226.05 Pubchem ID :66727148
Synonyms :

Safety of [ 1258833-77-0 ]

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

Application In Synthesis of [ 1258833-77-0 ]

* 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 [ 1258833-77-0 ]

[ 1258833-77-0 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 57848-46-1 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / Dean-Stark; Reflux 2: triethylamine; dmap / dichloromethane / 24 h / 20 °C 3: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
Multi-step reaction with 3 steps 1.1: toluene / Reflux 1.2: 12 h / 0 - 20 °C 2.1: triethylamine; dmap / dichloromethane / 24 h / 20 °C 3.1: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
Multi-step reaction with 4 steps 1: toluene / 16 h / Reflux; Dean-Stark 2: sodium tetrahydridoborate / methanol / 4 h / 20 °C / Cooling with ice 3: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 4: Aluminum Chloride / dichloromethane / 20 °C / Schlenk technique; Cooling with ice
Multi-step reaction with 4 steps 1: toluene / 16 h / 140 °C 2: methanol; sodium tetrahydridoborate / 0 - 20 °C 3: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 4: Aluminum Chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

  • 2
  • [ 1183945-15-4 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 24 h / 20 °C 2: Aluminum Chloride / dichloromethane / 29 h / -5 - 20 °C
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 2: Aluminum Chloride / dichloromethane / 20 °C / Schlenk technique; Cooling with ice
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 2: Aluminum Chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
  • 3
  • [ 1613147-80-0 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
32% With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 29h; 14.3 Step 3) 6-bromo-8-fluoroisoquinoline To a suspension of aluminium chloride (2 g, 15 mmol) in DCM (15 mL) was added N-(4-bromo-2-fluorobenzyl)-N-(2,2-dimethoxyethyl)benzenesulfonamide (1.3 g, 3 mmol) in DCM (15 mL) at -5 °C. The reaction was stirred at rt for 29 h, then quenched with 10% HC1 at -10 °C, and extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a yellow solid (0.22 g, 32%). MS (ESI, pos. ion) m/z: 226 [M + H]+; NMR (400 MHz, i/6-DMSO) δ (ppm): 9.48 (s, 1H), 8.63-8.62 (d, J= 5.6 Hz, 1H), 7.81 (s, 1H), 7.58-7.57 (d, J= 5.6 Hz, 1H), 7.40-7.38 (dd, J= 1.6 Hz, 9.6 Hz, 1H).
32% With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 29h; 14.3 Step 3) Preparation of 6-bromo-8-fluoroisoquinoline Aluminum trichloride (2.0 g, 15 mmol)Was suspended in dichloromethane (15 mL)The solution was cooled to -5 ° C,To this was added N- (4-bromo-2-fluorobenzyl) -N- (2,2-dimethoxyethyl) benzenesulfonamide (1.3 g, 3 mmol)In dichloromethane (15 mL).The reaction solution was stirred at room temperature for 29 hours,Cooled to -10 ° C,Plus 10% hydrochloric acid quenching,And extracted with dichloromethane (20 mL x 3)take. The combined organic phases were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column(Petroleum ether / ethyl acetate (v / v) = 3/1)The title compound was obtained as a yellow solid (0.22 g, 32%).
  • 4
  • [ 1258833-77-0 ]
  • [ 1339780-81-2 ]
YieldReaction ConditionsOperation in experiment
98% With sodium tetrahydridoborate In glacial acetic acid at 20℃; for 3h; 14.4 Step 4) 6-bromo-8-fluoro-1,2,3,4-tetrahydroisoquinoline To a solution of 6-bromo-8-fluoroisoquinoline (0.22 g, 0.97 mmol) in HOAc (5 mL) was added NaBH4 (129 mg, 3.41 mmol) in portions. The reaction was stirred at rt for 3 h, then treated with saturated aqueous aHC03 until pH 8 and extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20 mL), dried over anhydrous Na2S04, filtered, concentrated in vacuo, and dried in vacuo to afford the title compound as a yellow solid (0.22 g, 98%). MS (ESI, pos. ion) m/z: 230 [M + H]+; NMR (400 MHz, i/6-DMSO) δ (ppm): 7.26-7.23 (dd, J= 1.6 Hz, 9.2 Hz, 1H), 7.17 (s, 1H), 3.75 (s, 2H), 2.89-2.86 (t, J= 6.0 Hz, 2H), 2.68-2.65 (t, J= 5.6 Hz, 2H).
98% With sodium tetrahydridoborate; glacial acetic acid at 20℃; for 3h; 14.4 Step 4) Preparation of 6-bromo-8-fluoro-1,2,3,4-tetrahydroisoquinoline 6-bromo-8-fluoroisoquinoline (0.22 g, 0.97 mmol)Was dissolved in acetic acid (5 mL)To this was added sodium borohydride (129 mg, 3.41 mmol) in portions.The reaction solution was stirred at room temperature for 3 hours,After adjusting the pH to 8 with saturated sodium bicarbonate solution,Extraction with dichloromethane (20 mL x3).The combined organic phases were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and dried in vacuo.The title compound was obtained as a yellow solid (0.22 g, 98%).
With sodium tetrahydridoborate; glacial acetic acid In tetrahydrofuran at 20℃; for 4h; Cooling with ice;
With sodium tetrahydridoborate; glacial acetic acid at 0 - 20℃; Inert atmosphere; 8.5 Step 5. Compound 7 Compound 6 (2.6 g, 11.5 mmol, 1.0 eq) was dissolved in acetic acid (40 mL), and the temperature was lowered to 0 °C under nitrogen protection, and sodium borohydride (1.3 g, 34.5 mmol, 3.0 eq) was added.The reaction solution was warmed to room temperature and stirred for 2 hours, diluted with water (200 mL), cooled to 0° C., adjusted to pH 10 with sodium carbonate, and extracted with ethyl acetate (3×200 mL).The combined organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to obtain crude compound 7 (3.0 g), which was used in the next reaction without purification.

  • 5
  • [ 1258833-77-0 ]
  • [ 1613147-81-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydridoborate / glacial acetic acid / 3 h / 20 °C 2: anhydrous sodium carbonate / tetrahydrofuran; water monomer / 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydridoborate; glacial acetic acid / 3 h / 20 °C 2: anhydrous sodium carbonate / tetrahydrofuran; water monomer / 20 °C
Multi-step reaction with 2 steps 1: glacial acetic acid; sodium tetrahydridoborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydridoborate; glacial acetic acid / 0 - 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

  • 6
  • [ 1258833-77-0 ]
  • [ 1613147-82-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere
  • 7
  • [ 1258833-77-0 ]
  • [ 1613147-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,2-dimethoxyethane; water / 7 h / 95 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / water; 1,2-dimethoxyethane / 7 h / 95 °C / Inert atmosphere
  • 8
  • [ 1258833-77-0 ]
  • [ 1613147-79-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,2-dimethoxyethane; water / 7 h / 95 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: sodium tetrahydroborate; acetic acid / 3 h / 20 °C 2: sodium carbonate / tetrahydrofuran; water / 20 °C 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / water; 1,2-dimethoxyethane / 7 h / 95 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 4 h / 0 - 20 °C
  • 9
  • [ 2013582-59-5 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 80 °C 2: aluminum (III) chloride / dichloromethane / 16 h / -5 - 20 °C
  • 10
  • [ 2013582-60-8 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
31% With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 16h; Synthesis of compound 9-d At -5°C, compound 9-e (1.50mg, 3.18mmol) was added to a mixture of AlCl3 (2.0g, 15mmol) in DCM (20mL).The mixture was reacted for 16hrs at room temperature, followed by adding 2M HCl aqueous solution (20mL), extractedwith DCM (30mL33). The organic phases were combined, washed in turn with water (10mL33) and saturated brine(20mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue waspurified by silica column chromatography (PE:EA = 7:1) to give compound 9-d (220mg, yield 31%). LC-MS (ESI): m/z= 226 [M+H]+.
  • 11
  • [ 1258833-77-0 ]
  • [ 2013582-61-9 ]
YieldReaction ConditionsOperation in experiment
64% With N-iodo-succinimide; acetic acid; trifluoroacetic acid at 80℃; for 6h; Synthesis of compound 9-c Compound 9-d (200mg, 0.89mmol) and N-iodosuccinimide (300mg, 1.33mmol) were dissolved in acetic acid (10mL) and trifluoroacetic acid (2mL), the mixture was reacted for 6hrs at 80 °C. The mixture was cooled to roomtemperature, concentrated under reduced pressure to remove the solvent. The residue was purified by silica columnchromatography (PE:EA = 8:1) to give compound 9-c (200mg, yield 64%). LC-MS (ESI): m/z = 352 [M+H]+.
  • 12
  • [ 1258833-77-0 ]
  • [ 2013582-62-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide; acetic acid; trifluoroacetic acid / 6 h / 80 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 4 h / 50 °C / Inert atmosphere
  • 13
  • [ 1258833-77-0 ]
  • [ 2013582-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-iodo-succinimide; acetic acid; trifluoroacetic acid / 6 h / 80 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 4 h / 50 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere
  • 14
  • [ 1258833-77-0 ]
  • [ 2013581-84-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-iodo-succinimide; acetic acid; trifluoroacetic acid / 6 h / 80 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 4 h / 50 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: water; lithium hydroxide / methanol; tetrahydrofuran / 16 h / 20 °C
  • 15
  • [ 112734-22-2 ]
  • 6-bromo-8-fluoroisoquinoline [ No CAS ]
  • 16
  • [ 1258833-77-0 ]
  • [ 2243150-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 17
  • [ 1258833-77-0 ]
  • [ 2243146-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 18
  • [ 1258833-77-0 ]
  • [ 2243391-28-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 19
  • [ 1258833-77-0 ]
  • [ 2243391-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 20
  • [ 1258833-77-0 ]
  • [ 2243146-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 21
  • [ 1258833-77-0 ]
  • [ 2243391-42-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 22
  • [ 1258833-77-0 ]
  • [ 2243142-42-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 23
  • [ 1258833-77-0 ]
  • [ 2243151-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 24
  • [ 1258833-77-0 ]
  • [ 2243142-63-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 25
  • [ 1258833-77-0 ]
  • [ 2243143-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 26
  • [ 1258833-77-0 ]
  • [ 2243391-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 27
  • [ 1258833-77-0 ]
  • [ 2243391-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 28
  • [ 1258833-77-0 ]
  • [ 2243146-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 29
  • [ 1258833-77-0 ]
  • [ 2243151-23-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 30
  • [ 1258833-77-0 ]
  • [ 2243143-47-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 31
  • [ 1258833-77-0 ]
  • [ 2243143-60-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 32
  • [ 1258833-77-0 ]
  • [ 2243143-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 33
  • [ 1258833-77-0 ]
  • [ 2243151-38-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 34
  • [ 1258833-77-0 ]
  • [ 2243151-27-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 35
  • [ 1258833-77-0 ]
  • [ 2243154-53-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 36
  • [ 1258833-77-0 ]
  • [ 2243150-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 37
  • [ 1258833-77-0 ]
  • [ 2243144-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C
  • 38
  • [ 1258833-77-0 ]
  • [ 2243144-28-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: triethylamine / dichloromethane / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 39
  • [ 1258833-77-0 ]
  • [ 2243153-62-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h
  • 40
  • [ 1258833-77-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4.1: trichloroisocyanuric acid / water; acetonitrile / 0.5 h / 20 °C 4.2: 1 h / 0 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h 6.1: dichloromethane / 1 h / 20 °C
  • 41
  • [ 1258833-77-0 ]
  • [ 1627099-45-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 3: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere
  • 42
  • [ 1627099-56-2 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydridoborate / methanol / 4 h / 20 °C / Cooling with ice 2: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 3: Aluminum Chloride / dichloromethane / 20 °C / Schlenk technique; Cooling with ice
Multi-step reaction with 3 steps 1: methanol; sodium tetrahydridoborate / 0 - 20 °C 2: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 3: Aluminum Chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
  • 43
  • [ 1627099-44-8 ]
  • [ 1258833-77-0 ]
YieldReaction ConditionsOperation in experiment
47% With Aluminum Chloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; 8.4 Step 4. Compound 6 Dichloromethane (300 mL) was added to a reaction flask containing aluminum trichloride (22.0 g, 165 mmol, 6.7 eq), the temperature was lowered to 0°C under nitrogen protection, and compound 5 (11.0 g, 24.65 mmol, 1.0 eq) in dichloromethane (100 vmL).The reaction solution was warmed to room temperature and stirred for 16 hours, then quenched with ice water (100 mL), the pH value of the solution was adjusted to 10 with ammonia water, and the aqueous phase was extracted with dichloromethane (200 mL).The combined organic phases were dried over anhydrous sodium sulfate, and the residue obtained after concentration was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1) to obtain compound 6 (2.6 g, yield 47%).
41% With Aluminum Chloride In dichloromethane at 20℃; Schlenk technique; Cooling with ice;
  • 44
  • [ 1258833-77-0 ]
  • [ 13682-77-4 ]
  • [ 2642339-53-3 ]
YieldReaction ConditionsOperation in experiment
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In ethanol at 80℃; for 16h; D Step D, Preparation of 8-fluoro-6-vinylisoquinoHne. To a solution of 6-bromo-8- fuoroisoquinolme (1.17 g, 5.17 mmol, 1 equiv) in EtOH (35 mL) was added potassium tnfluoro(vinyl)borate (970.0 mg, 7.24 mmol, 1.5 equiv), PdCh(dppf) (171.0 mg, 0.21 mmol, 0.04 equiv), and EtsN (1.8 mL, 12.9 mmol, 2.5 equiv). The mixture was stirred at 80 °C for 16 h then concentrated. The residue was dissolved m EtOAc and washed with brine/ ater, dried (NazSiH), filtered, and concentrated. The residue was purified by flash chromatography (Combi-flash Rf, Hex/EtOAc :::: 0-40% gradient) to afford the title compound (800 mg, 4.6 mmol, 89% yield). NMR (400 MHz, Chloroform-*/) d 9.47 (s, IH), 8.58 (d, J = 5.6 Hz, 1H), 7.62 (d, J = 6.0 Hz, 111). 7.51 (s, IH), 7.39 (dd, J = 1.2, 11.6 Hz, 111). 6.86 (dd, J= 10.8, 17.6 Hz, 1H), 5.93 (d, J = 17.6 Hz, IH), 5.50 (d, J= 10.8 Hz, 1H).
  • 45
  • [ 770697-94-4 ]
  • [ 1258833-77-0 ]
  • [ 2375194-61-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis-(triphenylphosphine)-palladium In N,N-dimethyl acetamide at 150℃; for 1h; Inert atmosphere; 13; 137 8-fluoroisoquinoline-6-carbonitrile (13b) To a solution of 6-bromo-8- fluoroisoquinoline (13a, 700 mg, 3.10 mmol, 1 eq) in DMF (10 mL) was added Zn(CN)2 (545.45 mg,4.65 mmol, 294.84 uL, 1.5 eq) and Pd(PPh3)4 (357.85 mg, 309.67 umol, 0.1 eq). The mixture was stirred at 150°C for 1 hour under M.W. under N2. TLC (Petroleum ether: Ethyl acetate = 3:1) indicated of 13a was consumed completely, and one major new spot was formed. The mixture was quenched with saturated NaHCO3 until pH > 8, and extracted with ethyl acetate (80 mL*3), the combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 10:1 to 3:1) to give 13b as a yellow solid
  • 46
  • [ 1258833-77-0 ]
  • [ 2762504-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: potassium-t-butoxide; palladium diacetate; 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 3 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: potassium carbonate / acetonitrile / 3 h / 50 °C
Multi-step reaction with 6 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 16 h / 100 °C / Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 25 °C / 775.74 Torr 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: potassium carbonate / acetonitrile / 3 h / 50 °C
  • 47
  • [ 1258833-77-0 ]
  • [ 2762503-34-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: potassium-t-butoxide; palladium diacetate; 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 3 h / 100 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 16 h / 100 °C / Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 25 °C / 775.74 Torr
  • 48
  • [ 1258833-77-0 ]
  • [ 2762503-35-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: potassium-t-butoxide; palladium diacetate; 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 3 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
Multi-step reaction with 5 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 16 h / 100 °C / Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 25 °C / 775.74 Torr 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 49
  • [ 1258833-77-0 ]
  • [ 2762503-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: potassium-t-butoxide; palladium diacetate; 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 3 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: potassium carbonate / acetonitrile / 16 h / 50 °C
Multi-step reaction with 6 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 16 h / 100 °C / Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 25 °C / 775.74 Torr 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: potassium carbonate / acetonitrile / 16 h / 50 °C
  • 50
  • [ 1258833-77-0 ]
  • [ 2762501-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: potassium-t-butoxide; palladium diacetate; 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 3 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: potassium carbonate / acetonitrile / 16 h / 50 °C 6: lithium hydroxyde monohydrate; water monomer / tetrahydrofuran / 16 h / 20 °C
Multi-step reaction with 7 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl acetamide / 1 h / 150 °C / Inert atmosphere 2: acetic acid; sodium tetrahydridoborate / 5 h / 0 - 20 °C 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / toluene / 16 h / 100 °C / Inert atmosphere 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 25 °C / 775.74 Torr 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: potassium carbonate / acetonitrile / 16 h / 50 °C 7: lithium hydroxyde monohydrate; water monomer / tetrahydrofuran / 16 h / 20 °C
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