Potassium Carbonate → HCID 59300819, compound

HRID 2235388Notes

Reaction equation

HRID 2235388 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].Cl[CH2:21][C:22]1[CH:23]=[C:24]([F:33])[C:25]([O:29][CH:30]([CH3:32])[CH3:31])=[C:26]([F:28])[CH:27]=1.C([O-])([O-])=O.[K+].[K+]>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][C:22]1[CH:23]=[C:24]([F:33])[C:25]([O:29][CH:30]([CH3:31])[CH3:32])=[C:26]([F:28])[CH:27]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamideHCID 67427354HCID 67427354, compound

Product 1

HCID 59300819HCID 59300819, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.17 g) is alkylated using 5-chloromethyl-1,3-difluoro-2-isopropoxy-benzene (0.15 g; 0.68 mmol) and K2CO3 (0.3 g; 2.16 mmol) at RT for 18 h. After aqueous work-up the crude material (0.27 g) is de-acetylated in hydrochloric acid (30 ml; 6 N) at reflux. After aqueous work-up 5-amino-1-(3,5-difluoro-4-isopropoxy-benzyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.20 g) is obtained and used without further purification.

Workup

  1. customat RT
  2. customfor 18 h
  3. temperatureat reflux

Sources & evidence

ORD record
ord-26ffc3dc195c429ab36cd25a29ec856c
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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