Potassium Carbonate → HCID 59300741, compound

HRID 2235371Notes

Reaction equation

HRID 2235371 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][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>>[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]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 124940911-Bromo-4,4-dimethylpent-2-yneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300741HCID 59300741, compoundYield 23.1%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (10.5 g) is alkylated using 1-bromo-4,4-dimethyl-pent-2-yne (7 g; 40 mmol) and K2CO3 (5.52 g; 40 mmol) at 40° C. for 16 h. After aqueous work-up and purification by RP chromatography the pure material (3.9 g) is de-acetylated in MeOH (250 ml) using DBU (3.58 g) at reflux. After aqueous work-up 5-amino-1-(4,4-dimethyl-pent-2-ynyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (2.9 g) is obtained and used without further purification.

Workup

  1. customat 40° C.
  2. customfor 16 h
  3. customAfter aqueous work-up and purification by RP chromatography the pure material (3.9 g)
  4. temperatureat reflux

Sources & evidence

ORD record
ord-0689a4e1e5e14e61a87e4a81080bd77c
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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