Isopropyl iodide → 5-Isopropylamino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one

HRID 2235458Notes

Reaction equation

HRID 2235458 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][CH2:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:21])[CH3:20].I[CH:23]([CH3:25])[CH3:24].CC([O-])(C)C.[K+].C(Cl)Cl.CO>CN(C)C=O>[CH:23]([NH: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][CH2:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:20])[CH3:21])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 178027445-Amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-oneHCID 21226129Dichloromethane methanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 674274925-Isopropylamino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A8 (0.5 g) is alkylated using 2-iodopropane (0.5 ml; 5 mmol) and KOtBu (561 mg; 5 mmol) in N,N-dimethylformamide (7 ml) for 20 h at RT. After aqueous work-up and flash chromatography on silica gel eluting with CH2Cl2/MeOH (98:2) the compound (200 mg) is obtained.

Workup

  1. customfor 20 h
  2. customat RT

Sources & evidence

ORD record
ord-5f6103573be5451189778331726472e7
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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