3-Methyl-4-pyridinamine → 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methyl-pyridin-4-yl)amide

HRID 564736Notes

Reaction equation

HRID 564736 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N+](C1C=CC([O:28][C:29]([C:31]2[C:32]3[CH:41]=[C:40]([CH2:42][CH3:43])[O:39][C:33]=3[C:34]([O:37][CH3:38])=[N:35][CH:36]=2)=O)=CC=1)([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[C:32]2[CH:41]=[C:40]([CH2:42][CH3:43])[O:39][C:33]=2[C:34]([O:37][CH3:38])=[N:35][CH:36]=1)=[O:28]

Participants

5

Reactant 3

HCID 748113-Methyl-4-pyridinamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 541193452-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 540972802-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methyl-pyridin-4-yl)amideYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-3-methylpyridine (76 mg) in dry N,N-dimethylformamide (20 ml) was stirred at 0° C. under an atmosphere of dry nitrogen. Sodium bis(trimethylsilyl)amide (1.0M solution in tetrahydrofuran, 0.77 ml) was added and stirring continued at 0° C. for 10 minutes. 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) was added and stirring continued at room temperature for 90 minutes. The solvent was then removed in vacuo, the residue taken up in water (100 ml) and extracted with ethyl acetate (3×75 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 ethyl acetate followed by trituration with diethyl ether gave the title compound (66 mg) as a white solid.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 90 minutes
  3. customThe solvent was then removed in vacuo
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe combined organic extracts were washed with water (100 ml)
  6. dry with materialbrine (50 ml), dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification by column chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-c32e2dc40a06489ea8f0359f84e7a8d1
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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