Water → HCID 68281577, compound

HRID 2278593Notes

Reaction equation

Cl.C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C.Br[C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[N:34]([CH2:38][C:39]([CH3:41])=[CH2:40])[C:35](=[O:37])[CH3:36].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:27]=1[C:39]([CH3:41])([CH3:40])[CH2:38][N:34]2[C:35](=[O:37])[CH3:36]

Participants

Conditions

Temperature: 100 °C

Procedure

59 mg of palladium acetate, 1.5 g of tetrabutylammonium hydrochloride and 1.8 ml of triethylamine are added to a solution of 1.5 g of N-(2-bromo-3-fluorophenyl)-N-(2-methylallyl)acetamide in 10 ml of N,N-dimethylformamide. The reaction mixture is heated at 100° C. under an argon atmosphere for 16 hours. After cooling, 50 ml of water are added and the mixture is extracted with ethyl acetate. The organic phase is then washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (50/50: v/v), so as to give 520 mg of 1-(4-fluoro-3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone in the form of a yellow oil.

Workup

temperatureAfter cooling
extractionthe mixture is extracted with ethyl acetate
washThe organic phase is then washed with water
dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by silica column chromatography, elution
additionbeing carried out with a mixture of heptane and ethyl acetate (50/50: v/v)

Sources & evidence

ORD record: ord-60568b451da64059a9f41334e396e03b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133168B2

Reaction notes

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