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

HRID 336478Notes

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

Conditions

Temperature: 80 °C

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° C. 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

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

Sources & evidence

ORD record: ord-bb8f1b3dbbd94384b14453b753a9a689
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889691B2

Reaction notes

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