Pyridine → 2-[5-(7-Nitro-1H-indol-2-yl)-[1,2,4]oxadiazol-3-yl]-acetic acid methyl ester

HRID 1515274Notes

Reaction equation

HRID 1515274 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5](=[N:21][OH:22])[NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])=O.N1C=CC=CC=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[N:6]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[N+:18]([O-:20])=[O:19])[O:22][N:21]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 1363372013-(Hydroxyimino)-3-[(7-nitro-1H-indole-2-carbonyl)-amino]-propionic acid methyl ester

Product 1

HCID 1363372022-[5-(7-Nitro-1H-indol-2-yl)-[1,2,4]oxadiazol-3-yl]-acetic acid methyl esterYield 274.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Hydroxyimino)-3-[(7-nitro-1H-indole-2-carbonyl)-amino]-propionic acid methyl ester (960 mg, 1 mmol) prepared in Step B was dissolved in DMF (10 mL). Pyridine (1 mL) was added thereto, and the mixture was stirred for 4 h at 80°. The reaction was quenched by aqueous NH4Cl solution. The reaction mixture was extracted with EtOAc, and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (830 mg, Yield 90%).

Workup

  1. customThe reaction was quenched by aqueous NH4Cl solution
  2. extractionThe reaction mixture was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-15d4102b9194483e99d1a7b47a71e0a9
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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