Sodium Iodide → HCID 10289015, compound

HRID 491792Notes

Reaction equation

HRID 491792 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)=[O:20])=[O:8])[CH2:3][CH2:2]1.Cl.Cl[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[N:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:1]2[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[O:12][C:11]=3[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=3)=[O:20])=[O:8])[CH2:3][CH2:2]2)=[CH:33][CH:34]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 516892Sodium BicarbonateHCID 23062699HCID 23062699, compound

Product 1

HCID 10289015HCID 10289015, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-((Piperidin-4-yl)carbonylamino)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 228 is suspended in N,N-dimethylacetamide (3 ml), and thereto are added 4-(chloromethyl)pyridine hydrochloride (45 mg), sodium carbonate (80 mg) and sodium iodide (41 mg), and the mixture is stirred at room temperature for 12 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and a saturated brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, then 1/1) to give the title compound (109 mg).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materiala saturated brine, and dried over sodium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-fe96bd092090448ebb05c54e67536104
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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