Potassium Carbonate → HCID 59300940, compound

HRID 2235367Notes

Reaction equation

HRID 2235367 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].I[CH2:21][C:22]([F:25])([F:24])[F:23].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]([F:25])([F:24])[F:23])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300940HCID 59300940, compoundYield 58%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (5 g) is alkylated in a high pressure reaction vessel using 2-iodo-1,1,1-trifluoro-ethane (5.7 ml; 38 mmol) and K2CO3 (5.25 g; 38 mmol) at 50° C. for 14 days. After aqueous work-up and purification by RP chromatography the pure material (4 g) is de-acetylated in MeOH (150 ml) using DBU (3.6 ml) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-(2,2,2-trifluoro-ethyl)-1,3-dihydro-indol-2-one (3,34 g) is obtained and used without further purification.

Workup

  1. customat 50° C.
  2. customfor 14 days
  3. customAfter aqueous work-up and purification by RP chromatography the pure material (4 g)
  4. temperatureat reflux

Sources & evidence

ORD record
ord-ecbcb3ee57744a7ca8a8553e2e589268
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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