Potassium Carbonate → HCID 59300929, compound

HRID 2235373Notes

Reaction equation

HRID 2235373 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]#[N:25].C([O-])([O-])=O.[K+].[K+].C1CCN2C(=NCCC2)CC1>CO>[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]#[N:25])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300929HCID 59300929, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.24 g) is alkylated using 4-bromobutyronitrile (0.1 ml; 1 mmol) and K2CO3 (0.28 g; 2 mmol) at 50° C. for 3 days. After aqueous work-up the crude material (0.4 g) is de-acetylated in MeOH (10 ml) using DBU (0.1 ml) at RT in 3 h. After aqueous work-up 4-(5-amino-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-indol-1-yl)-butyronitrile (0.33 g) is obtained and used without further purification.

Workup

  1. customat 50° C.
  2. customfor 3 days
  3. customat RT
  4. customin 3 h

Sources & evidence

ORD record
ord-9c7a342591dc4dc0a908ff9150549914
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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