Potassium Carbonate → HCID 59300788, compound

HRID 2235391Notes

Reaction equation

HRID 2235391 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[O:23][CH:24]=[CH:25][N:26]=1.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][C:22]1[O:23][CH:24]=[CH:25][N:26]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219575432-(Chloromethyl)-1,3-oxazoleHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300788HCID 59300788, compoundYield 94.9%

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 (1 g) is alkylated using 2-chloromethyl-oxazole (0.47 g; 4 mmol) and K2CO3 (1.1 g; 7.96 mmol) at RT for 18 h. After aqueous work-up the crude material (1.30 g) is de-acetylated in MeOH (30 ml) using DBU (280 μl) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-oxazol-2-ylmethyl-1,3-dihydro-indol-2-one (1.09 g) is obtained and used without further purification.

Workup

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

Sources & evidence

ORD record
ord-a7cd9b6aef6c42d0b1c544f5d06bbad8
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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