Butyl bromide → HCID 178450168, compound

HRID 2236626Notes

Reaction equation

HRID 2236626 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[NH:18][C:17](=[O:24])/[C:16]/2=[CH:25]\[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[NH:18][C:17](=[O:24])/[C:16]/2=[CH:25]\[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:2][CH2:3][CH2:4][CH3:5])=[C:30]([OH:35])[CH:29]=1

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 178518275HCID 178518275, compound

Product 1

HCID 178450168HCID 178450168, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromobutane (30.4 μl, 0.28 mmol) and tetrabutylammonium iodide (104 mg, 0.283 mmol) in anhydrous N,N-dimethylformamide (2 ML) is added 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 43 mg of a white solid. MS (ESI) m/z 444.1 (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-fd67cabb9ad2420798dcbe560cda9780
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…