Potassium Carbonate → HCID 23092644, compound

HRID 2235352Notes

Reaction equation

HRID 2235352 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Br[CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CO>CC(O)C.Cl>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 127015683-(3-Bromopropyl)pyridineHCID 21226129Dichloromethane methanolHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 23092644HCID 23092644, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1 g) is alkylated using 3-(3-bromo-propyl)-pyridine (3.04 g; 15.2 mmol) and K2CO3 (2.1 g; 15.2 mmol) at RT for 4 days. After aqueous work-up and flash chromatography on silica gel eluting with CH2Cl2/MeOH (30:1), the pure alkylated acetamide (425 mg; 1.11 mmol) is de-acetylated under reflux conditions in 2-propanol (1.2 ml) and hydrochloric acid (6 N; 3.7 ml). 5-Amino-3,3-dimethyl-6-nitro-1-(3-pyridin-3-yl-propyl)-1,3-dihydro-indol-2-one (319 mg) is obtained by aqueous work-up and used without further purification.

Workup

  1. customat RT
  2. customfor 4 days

Sources & evidence

ORD record
ord-a89b4ef5bcce48f695b7a8fd50acd57b
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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