Allyl acetate → Methyl 3-allyl-4,7-dimethylindole-2-carboxylate

HRID 361613Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[CH3:11])[NH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].C(O[CH2:21][CH:22]=[CH2:23])(=O)C.CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC>CN(C)C=O>[CH2:23]([C:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[CH3:11])[NH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14])[CH:22]=[CH2:21]

Participants

Conditions

Temperature: 120 °C

Procedure

Under nitrogen atmosphere, 1.00 g (3.54 mmol) of methyl 3-bromo-4,7-dimethylindole-2-carboxylate and 0.31 g (5.23 mmol) of dichloro [1,1-bis(diphenylphos-phino)ferrocene]palladium (PdCl2 (dppf)) were suspended in 4 ml of anhydrous dimethylformamide (DMF). Thereto were added 0.57 ml (5.32 mmol) of allyl acetate and 2.7 ml (5.32 mmol) of hexabutylditin. The reaction mixture was stirred at 120° C. for 90 minutes and then subjected to Celite filtration. The filtrate was extracted with chloroform. The extract was purified by silica gel column chromatography (chloroform:n-hexane=1:1 to 3:1) to provide 0.75 g of white crystals. Yield: 87%

Workup

filtrationsubjected to Celite filtration
extractionThe filtrate was extracted with chloroform
customThe extract was purified by silica gel column chromatography (chloroform:n-hexane=1:1 to 3:1)

Sources & evidence

ORD record: ord-1819abb030284808a9311fb6bb9e8ae9
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866594

Reaction notes

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