Water → HCID 9800504, compound

HRID 1108322Notes

Reaction equation

HRID 1108322 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[N+](C1C=CC([O:28][C:29]([C:31]2[CH:32]=[CH:33][C:34]([O:46][CH3:47])=[C:35]3[O:39][C:38]([S:40](=[O:45])(=[O:44])[N:41]([CH3:43])[CH3:42])=[CH:37][C:36]=23)=O)=CC=1)([O-])=O.O>CN(C)C=O>[CH3:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:46][CH3:47])=[C:35]2[O:39][C:38]([S:40](=[O:44])(=[O:45])[N:41]([CH3:43])[CH3:42])=[CH:37][C:36]=12)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 748113-Methyl-4-pyridinamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 53939334HCID 53939334, compound

Product 1

HCID 9800504HCID 9800504, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-amino-3-methylpyridine (200 mg) in dimethylformamide (8 ml) under an atmosphere of nitrogen at 0° C. was added sodium hexamethyldisilazide (1.0M solution in tetrahydrofuran, 1.9 ml). The reaction mixture was stirred at this temperature for 5 minutes. 2-Dimethylsulfamyl-7-methoxy-benzofuran-4-carboxylic acid 4-nitrophenyl ester (400 mg) was then added and stirring continued for 30 minutes. Water (10 ml) was added and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (150 ml), washed with water (3×50 ml) and washed with brine (50 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography eluting with 10% methanol in ethyl acetate afforded the title compound as a white solid (0.3 g).

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
  5. washwashed with water (3×50 ml)
  6. washwashed with brine (50 ml)
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by column chromatography
  11. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-cbffe5bb1028408cb5ed6868b776f390
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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