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Chemical Structure| 1255206-67-7 Chemical Structure| 1255206-67-7

Structure of 1255206-67-7

Chemical Structure| 1255206-67-7

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Product Details of [ 1255206-67-7 ]

CAS No. :1255206-67-7
Formula : C9H7BrO2
M.W : 227.06
SMILES Code : O=C1OCC2=C1C=CC(Br)=C2C
MDL No. :MFCD26401765
InChI Key :IRAKZLQFUGTIGE-UHFFFAOYSA-N
Pubchem ID :59568711

Safety of [ 1255206-67-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1255206-67-7 ]

* 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 [ 1255206-67-7 ]

[ 1255206-67-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1255206-67-7 ]
  • potassium vinyltrifluoroborate [ No CAS ]
  • [ 1255206-69-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; 5-Bromo-4-memyl-2-benzofuran-l(3H)-one (598 mgs 4.47 mmol), potassium vinyl trifluoroborate (507 mgs 2.23 mmmol), PdCl2(dppf)-CΗ2Cl2Adduct (182 mg, 0.223 rammol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mJL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 0C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 12Og Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4- methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.76 ( d, J = 8Hz, IH), 7.03(dd, J= 11, 17 Hz5 IH), 5.84 (d, J= 17 Hz5 IH)5 5.55 (d, J- 11 Hz, IH), 5.29 (s5 2H)5 2.34 (s, 3H). LC-MS: M+l= 175; tR = 2.42 min
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; 5-Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl tnfluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0- 80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, 7= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; 5-Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, and then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, and dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0- 80% ETOAC Hexane solvent system) to yield 5-ethenyl-4-memyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H)5 7,03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Step C: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield the title product. LC-MS: M+l= 175 at 2.42 retention time.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Step C: 5-ethenyl-4-methyl-2-benzofuran-U3H -one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield the title product. LC-MS: M+l= 175 at 2.42 retention time.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Inert atmosphere; Sealed tube; Microwave irradiation; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. LC-MS: M+l= 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Step A: 5-Ethenyl-4-methyl-2-benzofuran-l(3H)-one 5- Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Inert atmosphere; Microwave irradiation; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)-one [INTERMEDIATE 1 ] (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one. -NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, = 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Step A: 5-ethenyl-4-methyl-2-benzofuran-1 (3H)-one; 5-Bromo-4-methyl-2-benzofuran-1 (3H)one(598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCb(dppf)-CH2CbAdduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethylacetate, washed with brine twice, dried and evaporated to dryness. The crude product waspurified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. LC-MS: M+1= 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; 5 -Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAc/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1 , 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. -NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: M+l= 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Step A: 5-ethenvl-4-methyl-2-benzofuran- 1 (3Th-one: 5-Bromo-4-methyl-2-benzofuran- 1(311)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethylacetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-i(3H)-one. LC-MS: M+1= 175
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium yinyl trifluoroborate (507 mg, 2.23 mmmol), Pdcl2(dppf)- cH2cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 methanol in a 20 m microwaye tube. The tube was sealed and degassed, then heated to 140 c for20 min. Analysis by Lc-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and eyaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAc/Hexane solyent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz,cDcl3): ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55(d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); Lc-MS: M+1= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Step A: S -ethenyl-4-methyl-2-benzofuran- 1(311)-one: S -Bromo-4-methyl-2-benzofuran- 1(311)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g RediSep column and 0-80% EtOAC/Hexanesolvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. ‘H-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+1= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; S-Bromo-4-methyl-2-benzofuran-i(311)-one (598 mg, 4.47 mmol), potassium vinyltrifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2C12 adduct (182 mg, 0.223 mmmol),and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4- methyl-2-benzofuran-1(3H)-one. lH-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J = 8Hz, 1H),7.03(dd, J 11, 17Hz, 1H), 5.84 (d, J 17Hz, 1H), 5.55 (d, J 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s,3H); LC-MS: M+1= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol) and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for 20 min. Analysis by LC-LC/MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. ^-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-LC/MS: M+l= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Inert atmosphere; 5 -Bromo-4-methyl-2-benzofuran- 1 (311)-one (598 mg, 4.47 mmol), potassium vinyltrifluoroborate (507 mg, 2.23 mmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120gRedi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H] = 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Inert atmosphere; 5-Bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tubewas sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H]= 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Microwave irradiation; Inert atmosphere; Step A: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one .
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Step A: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC dppf)- CH2C12 adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; 5-Bromo-4-methyl-2-benzofuran-1 (3H) -one (598 mg, 4.47 mmol) (INTERMEDIATE 1) , potassium vinyl trifluoroborate (507 mg, 2.23 mmmol) , PdCl2 (dppf) -CH2Cl2 adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120gcolumn and 0-80 EtOAc/hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1 (3H) -one. 1H NMR (500 MHz, CDCl3) : δ ppm 7.76 (d, J 8Hz, 1H) , 7.03 (dd, J 11, 17 Hz, 1H) , 5.84 (d, J 17 Hz, 1H) , 5.55 (d, J 11 Hz, 1H) , 5.29 (s, 2H) , 2.34 (s, 3H) LC-MS: M+1 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Microwave irradiation; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h; 5-bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (182 mg, 0.223 mmmol),and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealedand degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixturewas diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product waspurified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system toyield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. LC-MS: M+1= 175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Step A: 5 -ethenyl-4-methyl-2-benzofuran- 1 (311)-one: 5 -Bromo-4-methyl-2-benzofuran- 1(31])-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz,CDC13): ö ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55(d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+1= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; 5-Bromo-4-methyl-2-benzofuran- 1 (3H)-one [INTERMEDIATE 11(600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmol), PdC12(dppf)-CH2C12 Adduct (180 mg, 0.220 mmol), and TEA (0.62 mE, 4.5 mmol) were added to 10 mE ethanol in a 20 mE microwave tube. The tube was sealed and degassed, then heated to 140 C. for 20 minutes. Analysis by EC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPEC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4- methyl-2-benzothran-1 (3H)-one.‘H-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J=8 Hz, 1H),7.03 (dd, J=11, 17 Hz, 1H), 5.84 (d, J=17 Hz, 1H), 5.55 (d,J=11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). EC-MS: [M+1]=175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Inert atmosphere; 5-Bromo-4-methyl-2-benzofuran- 1 (3H) one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCi2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g RediSep column and 0-80% EtOAc/hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCls): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1 , 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; 5-Bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmol), PdCl2(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C. for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120 g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H]+=175.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; [0237] 5-Bromo-4-methyl-2-benzofuran-1(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis byLC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried andevaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solventsystem) to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one.1H-NMR (500 MHz, CDCl3): δ ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J = 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d,J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+1] = 175.

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