3-[4-((E)-2-{4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenyl}-vinyl)-3,5-dimethyl-phenyl]-2,2-dimethyl-propionic acid methyl ester → 3-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester

HRID 1360805Notes

Reaction equation

HRID 1360805 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C:4]([CH3:38])([CH3:37])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:22][C:23]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)=[N:24][N:25]=3)=[CH:17][C:16]=2[N+:33]([O-])=O)=[C:8]([CH3:36])[CH:7]=1>P(OCC)(OCC)OCC>[CH3:1][O:2][C:3](=[O:39])[C:4]([CH3:38])([CH3:37])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:33][C:16]3[C:15]([CH:14]=2)=[CH:20][CH:19]=[C:18]([C:21]2[O:22][C:23]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)=[N:24][N:25]=2)[CH:17]=3)=[C:8]([CH3:36])[CH:7]=1

Participants

3

Reactant 1

HCID 669664153-[4-((E)-2-{4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenyl}-vinyl)-3,5-dimethyl-phenyl]-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 669667913-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

Slurry 3-[4-((E)-2-{4-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenyl}-vinyl)-3,5-dimethyl-phenyl]-2,2-dimethyl-propionic acid methyl ester (245 mg, 0.449 mmol) in triethyl phosphite (6 mL) and heat to 160° C. for 2 h under N2. Concentrate the reaction under reduced pressure. Purify the concentrate by silica gel chromatography (5-35% EtOAc/HEP) to afford 3-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester as a yellow solid: (M+H)+ 514.3.

Workup

  1. concentrationConcentrate
  2. customthe reaction under reduced pressure
  3. customPurify the
  4. concentrationconcentrate by silica gel chromatography (5-35% EtOAc/HEP)

Sources & evidence

ORD record
ord-f45bb190684d4429b3cb4e144e008b4d
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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