Sodium Iodide → HCID 68297436, compound

HRID 1410886Notes

Reaction equation

HRID 1410886 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=1[CH2:14]Br)=[O:4].[CH3:16][O:17][C:18](=[O:31])[CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=1[CH2:14][N:20]([CH2:19][C:18]([O:17][CH3:16])=[O:31])[S:21]([C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1)(=[O:23])=[O:22])=[O:4]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 68297659HCID 68297659, compound

Product 1

HCID 68297436HCID 68297436, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-bromo-2-bromomethyl-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (363 mg, 1.07 mmol), (toluene-4-sulfonylamino)-acetic acid methyl ester (260 mg, 1.07 mmol), sodium iodide (321 mg, 2.14 mmol) and potassium carbonate (296 mg, 2.14 mmol) in DMF (10 mL) was stirred at r.t. for 16 h. Brine (30 mL) was added and the mixture was extracted with EtOAc. The organic layer was washed with water and dried over MgSO4. After the solvent was evaporated in vacuo, the crude product was chromatographed (0-70% EtOAc/hexanes) to give 292 mg of the title compound. MS: (+) m/z 501.13, 503.08 (M+1, 79/81Br).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customAfter the solvent was evaporated in vacuo
  5. customthe crude product was chromatographed (0-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cbfda327a3aa41778473b2f9e7ea0869
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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