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[ CAS No. 1408089-23-5 ] {[proInfo.proName]}

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Chemical Structure| 1408089-23-5
Chemical Structure| 1408089-23-5
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Product Details of [ 1408089-23-5 ]

CAS No. :1408089-23-5 MDL No. :MFCD13181971
Formula : C14H18BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QFHIOYSELCPERT-UHFFFAOYSA-N
M.W : 259.11 Pubchem ID :70975061
Synonyms :

Safety of [ 1408089-23-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1408089-23-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1408089-23-5 ]

[ 1408089-23-5 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 151230-42-1 ]
  • [ 73183-34-3 ]
  • [ 1408089-23-5 ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 85.0℃; for 15.0h;Inert atmosphere; [001255] Part 2: A mixture of <strong>[151230-42-1]6-bromo-2-methylbenzo[d]oxazole</strong> (1.06 g, 5.0 mmol), 4,4,4?,4?,5 ,5 ,5?,5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) (1.40 g, 5.5 mmol), KOAc (1.47 g, 15 mmol) and Pd(dppf)C12.CH2C12 (122 mg, 0.15 mmol) in dioxane ( 8 mL) was degassed and heated under N2 at 85 C. After 15 hours, the mixture was diluted with EtOAc, filtered through celite and concentrated. The residue was chromatographed to give 2-methyl-6-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzo [d]oxazole as a light orange solid (1 .30 g, 100%), MS m/z 260.4 [M+H].
34% A suspension of <strong>[151230-42-1]6-bromo-2-methylbenzo[d]oxazole</strong> (1 equiv), bis(pinacolato)diboron (2 equiv), potassium acetate (3 equiv) in 1,4-dioxane was degassed with argon for 10 min. Then, 1,1?-bis(diphenylphosphino)ferrocene palladium (II) chloride dichloromethane adduct (0.05 equiv) was added and the solution was further degassed with argon for 10 min. The reaction mixture was heated at 110 C. overnight. The reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 100-200 mesh 0-10% ethyl acetate in n-hexane as eluent) to give the title compound. (Yield: 34%), MS (ESI) m/z 260 [M+1]1.
  • 2
  • [ 1408089-23-5 ]
  • 2-chloro-7-fluoro-4H-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]
  • 7-fluoro-2-(2-methylbenzo[d]oxazol-6-yl)-4H-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In dichloromethane; acetonitrile at 60℃; for 3.5h; Inert atmosphere; 14.3.A [00 1256] Part 3, Step A: A mixture of 2-chloro-7-fluoro-4H-pyrido [1 ,2-a]pyrimidin-4-one (0.436 g, 2.2 mmol), 2-methyl-6-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzo [d]oxazole (0.647 g, 2.5 mmol), Pd(dppf)C12 in DCM (90 mg, 0.11 mmol), K2C03 (2M, 3.0 mL, 6.Ommol), and ACN (6 mL) was degassed and then heated under N2 at 60 °C for 3.5 hours. The volatiles were removed and the residue was chromatographed (2.5% MeOH/CH2C12) to give 7-fluoro-2- (2-methylbenzo [d]oxazol-6-yl)-4H-pyrido [1 ,2-a]pyrimidin-4-one as an off-white solid (0.64 g, 98%). MS m/z 296.4 [M+H] ‘H NMR (500 MHz, DMSO-d6): ö 8.96-8.95 (1H, m), 8.51 (1H, d, J = 1.6 Hz), 8.26 (1H, dd, J 8.5 Hz, 1.6 Hz), 8.16-8.12 (1H, m), 7.91-7.88 (1H, m), 7.78 (1H, d, J = 8.4 Hz), 7.17 (1H, s), 2.67 (3H, s).
  • 3
  • [ 1408089-23-5 ]
  • [ 1404364-72-2 ]
  • [ 1618663-21-0 ]
YieldReaction ConditionsOperation in experiment
58% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 85℃; for 1.5h; 3 6-(2,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1 equiv), 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), sodium carbonate (3 equiv) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (0.04 equiv) were combined in a 5:1 mixture of 1,4-dioxane and water (0.27 M). The mixture was heated to 85° C. for 1.5 h. The crude product was purified on silica gel (0-10% ethyl acetate in petroleum ether) to give an impure brown oil. The product was purified on silica gel (0-20% ethyl acetate in petroleum ether) to give the title compound (58% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70 (d, J=8 Hz, 1H), 7.62 (s, 1H), 7.44 (m, 2H), 5.68 (s, 2H), 3.65 (m, 2H), 2.69 (s, 3H), 0.99 (m, 2H), 0.05 (s, 9H). MS (ESI) m/z 449.0 [M+1]+.
58% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 85℃; for 1.5h; Inert atmosphere;
  • 4
  • [ 1408089-23-5 ]
  • [ 1618663-45-8 ]
  • [ 1618663-46-9 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole; 2-chloro-5-iodo-4-(2-methoxyethoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine With sodium carbonate In 1,4-dioxane; water for 0.166667h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 75℃; Inert atmosphere; 13 6-(2-Chloro-4-(2-methoxyethoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole A solution of 2-chloro-5-iodo-4-(2-methoxyethoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-c]pyrimidine (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1 equiv) and sodium carbonate (2 equiv) in 1,4-dioxane:water (3:1, 0.05 M) was degassed with argon for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.1 equiv) was added and the solution was further degassed with argon for 10 min. The reaction mixture was heated at 75° C. overnight. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The reaction mixture was diluted with water and the compound was extracted in ethyl acetate. The organic layer was separated, dried over sodium sulfate, and purified by column chromatography (neutral silica gel 100-200 mesh, 0-3% MeOH in DCM as eluent) to afford the title compound (76% yield). MS (ESI) m/z 489 [M+1]+.
  • 5
  • [ 1408089-23-5 ]
  • [ 1618663-50-5 ]
  • [ 1618663-51-6 ]
YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate In 1,4-dioxane; water at 70℃; for 3h; 15A; 15B 4-((2-Chloro-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol To a degassed mixture of 4-((2-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1.2 equiv) and tripotassium phosphate trihydrate (3 equiv) in a 9:1 mixture of 1,4-dioxane and water (0.18 M) was added palladium 1,1-bis(diphenylphosphion)ferrocene dichloride (0.1 equiv). The reaction mixture was stirred at 70° C. for 3 h. After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-2% DCM in MeOH) to afford the title compound (95% yield) as a red oil. MS (ESI) m/z 543.2 [M+1]+.
  • 6
  • [ 1408089-23-5 ]
  • [ 1618663-78-7 ]
  • [ 1618663-79-8 ]
YieldReaction ConditionsOperation in experiment
49% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate In 1,4-dioxane; water at 70℃; for 2h; 26 6-(2-Chloro-4-(1-methylcyclobutoxy)-7-((2-(trimethylsilyl)-ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole To a degassed mixture of 2-chloro-5-iodo-4-(1-methylcyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1.1 equiv) and tripotassium phosphate trihydrorate (3.0 equiv) in a 9:1 mixture of 1,4-dioxane and water (0.45 M) was added palladium 1,1-bis(diphenylphosphion)-ferrocene dicholoride (0.1 equiv). The reaction mixture was stirred at 70° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-25% ethyl acetate in petroleum ether) to afford the title compound (49% yield) as a yellow solid. MS (ESI) m/z 499.2 [M+H]+.
  • 7
  • [ 1408089-23-5 ]
  • [ 1618663-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 120 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 120 °C
Multi-step reaction with 2 steps 1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 2: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 8
  • [ 1408089-23-5 ]
  • [ 1618663-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 70 °C
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C
  • 9
  • [ 1408089-23-5 ]
  • [ 1618663-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 70 °C 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 4 h / 110 °C
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 10
  • [ 1408089-23-5 ]
  • [ 1618663-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 5 h / 75 °C
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C
  • 11
  • [ 1408089-23-5 ]
  • [ 1618663-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 5 h / 75 °C 3: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 2 h / 150 °C / Microwave irradiation
  • 12
  • [ 1408089-23-5 ]
  • [ 1618663-44-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 5 h / 75 °C 3: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 2 h / 150 °C / Microwave irradiation
  • 13
  • [ 1408089-23-5 ]
  • [ 1618663-52-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 3 h / 70 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 14
  • [ 1408089-23-5 ]
  • [ 1618663-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 2: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 15
  • [ 1408089-23-5 ]
  • [ 1618663-57-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 16
  • [ 1408089-23-5 ]
  • [ 1618663-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 25 °C
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C
  • 17
  • [ 1408089-23-5 ]
  • [ 1618663-62-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,4-dioxane / 25 °C 3: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1.5 h / 140 °C / Sealed tube; Inert atmosphere
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 18
  • [ 1408089-23-5 ]
  • [ 1618663-71-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 19
  • [ 1408089-23-5 ]
  • [ 1618663-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 20
  • [ 1408089-23-5 ]
  • [ 1618662-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 90 °C
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 90 °C
  • 21
  • [ 1408089-23-5 ]
  • [ 1618663-80-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 70 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 22
  • [ 1408089-23-5 ]
  • [ 1618662-56-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 70 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 90 °C / Sealed tube
  • 23
  • [ 1408089-23-5 ]
  • [ 1672673-01-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 1 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 1 h / 100 °C
  • 24
  • [ 1408089-23-5 ]
  • [ 1618663-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 1 h / 110 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 1 h / 110 °C
  • 25
  • [ 1408089-23-5 ]
  • [ 1618663-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 26
  • [ 1408089-23-5 ]
  • [ 1618663-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 27
  • [ 1408089-23-5 ]
  • [ 1618663-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C
  • 28
  • [ 1408089-23-5 ]
  • [ 1618662-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 80 °C
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 80 °C
  • 29
  • [ 1408089-23-5 ]
  • [ 1618664-04-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 4 h / 100 °C
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 4 h / 100 °C
Multi-step reaction with 2 steps 1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 2: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 30
  • [ 1408089-23-5 ]
  • [ 1618664-05-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium hydride / mineral oil; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
  • 31
  • [ 1408089-23-5 ]
  • [ 1618664-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium hydride / mineral oil; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3: caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 3 h / 110 °C
  • 32
  • [ 1408089-23-5 ]
  • [ 1618663-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube
  • 33
  • [ 1408089-23-5 ]
  • [ 1618663-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 85 °C 2.1: sodium t-butanolate / 1,3-dioxane / 3 h / 70 °C / Inert atmosphere; Sealed tube 3.1: caesium carbonate / 1,4-dioxane / 0.17 h / Inert atmosphere 3.2: 6 h / 110 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate / 1,4-dioxane; water / 2 h / 90 °C 2.1: caesium carbonate / 1,4-dioxane / 0.17 h / Inert atmosphere 2.2: 6 h / 110 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 2: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 34
  • [ 1408089-23-5 ]
  • [ 1618663-33-4 ]
  • [ 1618663-22-1 ]
YieldReaction ConditionsOperation in experiment
42% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate In 1,4-dioxane; water at 90℃; for 2h; 7 6-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole To a mixture of 2-chloro-4-(cyclopentyloxy)-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzooxazole (1 equiv), tripotassium phosphate trihydrorate (3 equiv) in 1,4-dioxane and water (8:1, 0.5 M) was added 1,1-bis(diphenylphosphion)ferrocene palladium dichloride (0.1 equiv). The mixture was refluxed at 90° C. for 2 h. Filtration and concentration gave the crude product, which was purified by silica gel column chromatography (20% ethyl acetate in petroleum ether) to afford the title compound (42% yield). MS (ESI) m/z 498.2 [M+1]+.
40% In 1,4-dioxane; water at 75℃; for 15h; Alkaline conditions;
  • 35
  • [ 1408089-23-5 ]
  • 4-((4-cyclobutoxy-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 36
  • [ 1408089-23-5 ]
  • 4-((4-(2-hydroxyethoxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 37
  • [ 1408089-23-5 ]
  • 3-methoxy-N-methyl-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-(oxetan-3-yloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 38
  • [ 1408089-23-5 ]
  • (S)-3-methoxy-N-methyl-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-((tetrahydrofuran-3-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 39
  • [ 1408089-23-5 ]
  • 3-methoxy-N-methyl-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-((tetrahydro-2H-pyran-4-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 41
  • [ 1408089-23-5 ]
  • [ 1618660-48-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C
  • 42
  • [ 1408089-23-5 ]
  • [ 1618660-02-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2.1: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3.1: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 4.1: trifluoroacetic acid / dichloromethane / 20 °C 4.3: 20 - 50 °C
  • 43
  • [ 1408089-23-5 ]
  • [ 1618659-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2.1: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3.1: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 4.1: trifluoroacetic acid / dichloromethane / 20 °C 4.3: 20 - 50 °C
  • 44
  • [ 1408089-23-5 ]
  • [ 1618660-18-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2.1: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3.1: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 4.1: trifluoroacetic acid / dichloromethane / 20 °C 4.3: 20 - 50 °C
  • 45
  • [ 1408089-23-5 ]
  • [ 1618660-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 1.5 h / 85 °C / Inert atmosphere 2: sodium t-butanolate / 1,4-dioxane / 16 h / 25 °C 3: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C
  • 46
  • [ 1408089-23-5 ]
  • 6-azido-2-methylbenzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium azide; copper diacetate In methanol at 55℃; for 24h;
  • 47
  • [ 1408089-23-5 ]
  • C17H25BrN4O [ No CAS ]
  • [ 76-05-1 ]
  • (x)C2HF3O2*C25H31N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole; C17H25BrN4O With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: trifluoroacetic acid
  • 48
  • (E)-1-(2-methylbenzo[d]oxazol-6-yl)butan-1-one O-perfluorobenzoyl oxime [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1408089-23-5 ]
YieldReaction ConditionsOperation in experiment
68% With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube;
  • 49
  • C12H14N2O2 [ No CAS ]
  • [ 1408089-23-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube 2: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube
  • 50
  • C12H13NO2 [ No CAS ]
  • [ 1408089-23-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / Inert atmosphere; Sealed tube 2: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube 3: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube
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