Sodium hydride → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine4-carboxylic acid (3,5-dichloropyridin-4-yl)amide

HRID 564729Notes

Reaction equation

HRID 564729 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[N+](C1C=CC([O:21][C:22]([C:24]2[C:25]3[CH:34]=[C:33]([C:35](=[O:37])[CH3:36])[O:32][C:26]=3[C:27]([O:30][CH3:31])=[N:28][CH:29]=2)=O)=CC=1)([O-])=O>CN(C)C=O>[Cl:9][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:8])[C:2]=1[NH:1][C:22]([C:24]1[C:25]2[CH:34]=[C:33]([C:35](=[O:37])[CH3:36])[O:32][C:26]=2[C:27]([O:30][CH3:31])=[N:28][CH:29]=1)=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 541659832-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 97999942-Acetyl-7-methoxyfuro[2,3-c]pyridine4-carboxylic acid (3,5-dichloropyridin-4-yl)amideYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-3,5-dichloropyridine (57 mg) in dry N,N-dimethylformamide (10 ml) was stirred at room temperature under an atmosphere of dry nitrogen. Sodium hydride (21 mg) was added and stirring continued for 45 minutes. 2-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (100 mg) was added and the resulting mixture stirred overnight. The solvent was removed in vacuo, the residue taken up in water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (100 ml) then brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 50% hexane in ethyl acetate gave the title compound (12 mg) as a white solid.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customThe solvent was removed in vacuo
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic extracts were washed with water (100 ml)
  5. dry with materialbrine (50 ml), dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customPurification by column chromatography on silica eluting with 50% hexane in ethyl acetate

Sources & evidence

ORD record
ord-d43e9da2ff5742ddbcfef6d11021c5b8
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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