Cesium carbonate → Methyl 4-acetylamino-2-tert-butyl-5-phenyl-4-benzofuran-7-carboxylate

HRID 17541Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[O:13][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1Br)(=[O:3])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:12]([C:14]([CH3:16])([CH3:17])[CH3:15])[O:13][C:9]2[C:10]=1[C:11]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:7][C:8]=2[C:18]([O:20][CH3:21])=[O:19])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen atmosphere, methyl 4-acetylamino-5-bromo-2-tert-butyl-1-benzofuran-7-carboxylate (I-252) (147 mg, 0.4 mmol), phenylboronic acid (61 mg, 0.5 mmol), aqueous 2 M cesium carbonate solution (0.5 ml, 1.0 mmol) and tetrakistriphenylphosphine palladium(0) (23 mg, 0.02 mmol) were added, followed by stirring at 100° C. for 6 hours. After cooling to room temperature, ethyl acetate was added to the reaction liquid, followed by washing with saturated sodium bicarbonate water and saturated brine and drying over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane/ethyl acetate (2:1) gave the entitled compound (117 mg, 80%) as a white solid.

Workup

temperatureAfter cooling to room temperature
washby washing with saturated sodium bicarbonate water and saturated brine
dry with materialdrying over anhydrous magnesium sulfate
filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record: ord-d5fcb61674db4886b73a55d6a063ad14
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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