Acetone → HCID 11998015, compound

HRID 2102686Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.BrCC1C=C[CH:25]=[C:24]([CH2:28][F:29])C=1.[I-].[K+].[C:32](=O)([O-])[O-].[K+].[K+].[CH3:38][C:39]([CH3:41])=O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:38][C:39]3[CH:41]=[CH:25][CH:24]=[C:28]([F:29])[CH:32]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=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-methoxy-phenyl)-1,3-dihydro-indol-2-one (50 mg, 0.18 mmol) (from Example 6b supra), 1-bromomethyl-3-fluoromethyl-benzene (41 mg, 0.21 mmol) (Aldrich), potassium iodide (36 mg, 0.21 mmol) and potassium carbonate (54 mg, 0.39 mmol) in acetone (2 mL) was heated at 60° C. for 3 hours in a capped pressure tube. After cooling, mixture was diluted with ethyl acetate and extracted with water and brine. Aqueous layers were back washed with ethyl acetate. Organic layers were combined, dried (Na2SO4), filtered and concentrated. Residue was recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-(3-fluoro-benzyl)-3-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 25 mg, 36%).

Workup

temperatureAfter cooling
extractionextracted with water and brine
washAqueous layers were back washed with ethyl acetate
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customResidue was recrystallized from dichloromethane-hexanes

Sources & evidence

ORD record: ord-fabeaae3cd7843cfad8b6b24906a876d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576082B2

Reaction notes

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