Sodium Iodide → HCID 68553449, compound

HRID 402530Notes

Reaction equation

HRID 402530 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:18]=2[CH3:19])[C:15](=[O:20])[N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH:13]=[CH:12]3)[CH2:4][CH2:3]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][CH2:40][CH2:41][CH2:42]Br>CN(C=O)C.O>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:14]2[CH:13]=[CH:12][C:11]3[C:16](=[CH:17][C:18]([CH3:19])=[C:9]([O:8][CH:5]4[CH2:4][CH2:3][CH:2]([N:1]5[CH2:42][CH2:41][CH2:40][CH2:39]5)[CH2:7][CH2:6]4)[CH:10]=3)[C:15]2=[O:20])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178490765HCID 178490765, compound

Product 1

HCID 68553449HCID 68553449, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.4 g (1 mmol) of 6-(cis-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one (26, step b), 0.31 g (2 mmol) sodium iodide and 0.35 g (2.5 mmol) potassium carbonate in 40 ml DMF were added dropwise 0.24 g (1.1 mmol) 1,4-dibromobutane. After stirring at room temperature for 2 days the mixture was diluted with water and extracted with ethyl acetate. After drying and evaporation the residue was purified by chromatography to yield 182 mg of 2-(4-methoxy-benzyl)-7-methyl-6-(4-pyrrolidin-1-yl-cyclohexyloxy)-2H-isoquinolin-1-one.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter drying
  3. customevaporation the residue
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-167a8f228ecc488d96f29f95ded9548d
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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