Methyl iodide → N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-N-methyl-3-phenyl-propionamide

HRID 2235413Notes

Reaction equation

[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-:24])=[O:23])=[C:8]([NH:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:3]1=[O:30].[C:32]([O-])([O-])=O.[K+].[K+].CI>CN(C)C=O>[CH3:31][C:2]1([CH3:1])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-:24])=[O:23])=[C:8]([N:11]([CH3:32])[C:12](=[O:21])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:3]1=[O:30]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of N-(3,3-dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-phenyl-propionamide (142 mg) in dry N,N-dimethylformamide (6 ml) is added K2CO3 (163 mg; 1.18 mmol) and methyl iodide (45 μl; 0.72 mmol). The mixture is stirred at 75° C. for 2 days. After an aqueous work-up the compound is obtained.

Workup

customAfter an aqueous work-up the compound is obtained

Sources & evidence

ORD record: ord-99ce6d3f80434d1cb23d33bbc8185a3a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714010B2

Reaction notes

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