Potassium Carbonate → HCID 58017139, compound

HRID 883661Notes

Reaction equation

HRID 883661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 58017139HCID 58017139, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the general procedure as outlined above for the synthesis of intermediate 43, f 5-chloroisatin, compound VIII, (10.0 g, 55.07 mmol) was reacted with potassium carbonate (9.89 g, 5.03 mmol) and tert-butyl bromoacetate (8.95 ml, 60.58 mmol) in N,N-dimethylformamide (100 ml) to give the title compound (12.14 g, 75%) as orange solid (HPLC purity: 99%) after precipitation from water. MS (ESI−): 294.2

Sources & evidence

ORD record
ord-74f94e1d62de485689110cb37c1cc7ba
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

Loading…