2-Cyclohexen-1-one → Rac-6-chloro-3-(3-chloro-benzyl)-3-(3-oxo-cyclohexyl)-1,3-dihydro-indol-2-one

HRID 2102703Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:20]1(=[O:26])[CH2:25][CH2:24][CH2:23][CH:22]=[CH:21]1.N12CCCN=C1CCCCC2>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)([CH:22]3[CH2:23][CH2:24][CH2:25][C:20](=[O:26])[CH2:21]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (0.125 g, 0.49 mmol) (from Example 30b supra), 2-cyclohexen-1-one (0.047 g, 0.49 mmol) (Aldrich), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.37 g, 2.4 mmol) (Fluka AG) in methanol (20 mL) was heated at 60° C. for 2 hours. After cooling, the mixture was concentrated, diluted with water, extracted with ethyl acetate (2×100 mL). The organic layers were separated, washed with water and brine. Aqueous layers were back washed with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-hexanes, 2:3, V/V) to give rac-6-chloro-3-(3-chloro-benzyl)-3-(3-oxo-cyclohexyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 0.057 g, 30%).

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated
additiondiluted with water
extractionextracted with ethyl acetate (2×100 mL)
customThe organic layers were separated
washwashed with water and brine
washAqueous layers were back washed with ethyl acetate
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by chromatography (ethyl acetate-hexanes, 2:3, V/V)

Sources & evidence

ORD record: ord-a8c05bd8b8314869b094f9c25c1596e0
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576082B2

Reaction notes

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