1-Bromohexane → HCID 178444951, compound

HRID 2236628Notes

Reaction equation

HRID 2236628 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].[Br:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][C:19](=[O:26])/[C:18]/2=[CH:27]\[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][C:19](=[O:26])/[C:18]/2=[CH:27]\[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[C:32]([OH:37])[CH:31]=1

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 178518275HCID 178518275, compound

Product 1

HCID 178444951HCID 178444951, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromohexane (40.0 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 35 mg of a white solid. MS (ESI) m/z 472.5 (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-5d4cdb4704234b32acecf29543afaf18
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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