Allyl iodide → HCID 178458417, compound

HRID 2236627Notes

Reaction equation

HRID 2236627 reaction equation
[CH2:1](I)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[Br:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[NH:17][C:16](=[O:23])/[C:15]/2=[CH:24]\[NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([OH:34])[CH:28]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([O:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25]/[CH:24]=[C:15]2\[C:16](=[O:23])[NH:17][C:18](=[O:22])[C:19]3[C:14]\2=[CH:13][C:12]([Br:11])=[CH:21][CH:20]=3)=[CH:28][C:29]=1[OH:34])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 178518275HCID 178518275, compound

Product 1

HCID 178458417HCID 178458417, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of allyl iodide (25.6 μl, 0.28 mmol) and tetrabutylammonium iodide (104 mg, 0.283 mmol) in anhydrous N,N-dimethylformamide (2 ML) is added of potassium carbonate (207 mg, 1.5 mmol). The mixture stirred at room temperature and (4Z)-6-bromo-4-{[(3,4-dihydroxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (100 mg, 0.26 mmol) is added. After the mixture is stirred at 65° C. for 30 min, the resulting mixture is concentrated and the residue is then partitioned between water (20 ml) and ethyl acetate (20 ml). The organic layer is then dried and purified by high performance liquid chromatography to give 36 mg of a white solid. MS (ESI) m/z 428.6 (M+1).

Workup

  1. stirringAfter the mixture is stirred at 65° C. for 30 min
  2. concentrationthe resulting mixture is concentrated
  3. customthe residue is then partitioned between water (20 ml) and ethyl acetate (20 ml)
  4. customThe organic layer is then dried
  5. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-1553b2a9648e424d8619e31372e5dabf
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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