N-Iodosuccinimide → HCID 21949275, compound

HRID 2215603Notes

Reaction equation

HRID 2215603 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4].[I:22]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[C:20]([I:22])=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 21949243HCID 21949243, compound

Product 1

HCID 21949275HCID 21949275, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N1-Methyl-5-(2-amino-4-pyrimidyl)oxy-1H-1-indolecarboxamide (302 mg, 1.07 mmol) and N-iodosuccinimide (301 mg, 1.34 mmol) were dissolved in N,N-dimethylformamide (3.0 ml); and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with water and brine, and was dried over anhydrous magnesium sulfate. The solvent was distilled off; and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) to yield the title compound as yellow crystals (224 mg, 0.547 mmol, 51%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washand the organic layer was washed with water and brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customand the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-07f5810ba24f455c9506fb23f904bdcc
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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