Dimethyl Sulfoxide → HCID 68663743, compound

HRID 452726Notes

Reaction equation

Br[C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.C(N([CH2:22][CH3:23])CC)C.CS(C)=[O:26].[CH2:28]([OH:30])C>C(OCC)(=O)C>[CH3:16][C:13]1[O:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][CH:3]=[C:2]([C:28]([O:30][CH2:22][CH3:23])=[O:26])[C:6]=3[CH:7]=2)=[N:15][N:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole (837 mg, 3.00 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (245 mg, 0.300 mmol), triethylamine (0.836 mL, 6.00 mmol), dimethyl sulfoxide (6 mL) and ethanol (3 mL) was stirred under a carbon monoxide atmosphere at 100° C. for 10 hr. After cooling, the reaction mixture was diluted with ethyl acetate, and insoluble material was removed by filtration. The filtrate was washed with 1M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from ethyl acetate to give the title compound (379 mg, yield 46%) as colorless crystals.

Workup

temperatureAfter cooling
customwas removed by filtration
washThe filtrate was washed with 1M hydrochloric acid, water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-69bc5429eedd462c8ec7a584bcb07a4c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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