p-Anisoyl chloride → N-[3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide

HRID 2235417Notes

Reaction equation

HRID 2235417 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[N:7]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:6](=[O:19])[C:5]2([CH3:21])[CH3:20].[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl.CO>[CH3:20][C:5]1([CH3:21])[C:4]2[C:8](=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([NH:1][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[CH:3]=2)[N:7]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[C:6]1=[O:19]

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 230926665-Amino-3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 67425720N-[3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamideYield 27.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

N-[3,3-Dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide is prepared from A9 (419 mg) and 4-methoxy-benzoyl chloride (491 mg; 2.88 mmol) as described in Example 1a. N-[3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide (167 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (50:1)

Sources & evidence

ORD record
ord-16fc47c714314e07a6f3b7d56f589490
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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