Sodium Carbonate → 5-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 1850379Notes

Reaction equation

C(B1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])(C)[O:4]1)=C.C(=O)([O-])[O-].[Na+].[Na+].[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2OC(C)(C)[C:24](=O)[C:23]=2[C:30]=1Br>C(OCC)(=O)C.O.COCCOC.C(O)C>[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2[O:7][C:6]([CH3:8])([CH3:9])[C:5](=[O:4])[C:11]=2[C:30]=1[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 100 °C

Procedure

2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan (3.79 g, 24.6 mmol), tetrakistriphenyl phosphine palladium (605 mg, 0.523 mmol), sodium carbonate (1.36 g, 12.8 mmol), water (8 mL) and ethanol (5 mL) were added to a solution of DME (14 mL) containing 5-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (2.00 g, 7.04 mmol) synthesized in Reference Example 21, and the mixture was stirred under argon atmosphere at 100° C. for 45 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15) to give 1.47 g of the title compound (yield: 91%).

Workup

customsynthesized in Reference Example 21
temperatureAfter cooled to room temperature
customIt was dried
customAfter that, the solvent was removed under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15)

Sources & evidence

ORD record: ord-6425e6d07076452094f84243459d932a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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