O-Xylene → HCID 66760383, compound

HRID 2063800Notes

Reaction equation

C[C:2](C)([O-:4])C.[Na+].C[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1C.[N:15]1([C:22]2[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]3[O:29][C:28]([CH3:31])([CH3:30])[C:27](=[O:32])[C:26]=3[C:33]=2[CH3:34])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:2][O:4][C:13]1[CH:12]=[CH:11][C:10]([N:18]2[CH2:19][CH2:20][CH2:21][N:15]([C:22]3[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]4[O:29][C:28]([CH3:31])([CH3:30])[C:27](=[O:32])[C:26]=4[C:33]=3[CH3:34])[CH2:16][CH2:17]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Bis(tri-tert-butylphosphine)palladium (20.0 mg, 0.0387 mmol) and sodium tert-butoxide (500 mg, 5.16 mmol) were added to a solution of o-xylene (20 mL) containing 5-(1,4-diazepan-1-yl)-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one synthesized in Reference Example 63, and the mixture was stirred under argon atmosphere at 120° C. for 12 hours. After cooled to room temperature, the mixture was diluted with water and extracted 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 100:0 to 90:10) to give 240 mg of the title compound (yield: 45%).

Workup

customsynthesized in Reference Example 63
temperatureAfter cooled to room temperature
extractionextracted
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 100:0 to 90:10)

Sources & evidence

ORD record: ord-3a497e13ae7846f594ba6ae072a61fad
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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