Trimethyl phosphite → Benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate

HRID 1514955Notes

Reaction equation

HRID 1514955 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([CH3:13])[C:10](/[CH:14]=[CH:15]/[C:16]2[CH:31]=[CH:30][C:19]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[CH:18][C:17]=2[N+:32]([O-])=O)=[C:9]([CH3:35])[CH:8]=1)=[O:4].COP(OC)OC>>[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:32][C:17]3[C:16]([CH:15]=2)=[CH:31][CH:30]=[C:19]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH:18]=3)=[C:9]([CH3:35])[CH:8]=1)=[O:4]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 66966058Benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate

Product 1

HCID 66965810Benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate

Conditions

Temperature
110 °C

Procedure

A mixture of benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate (1.87 g, 3.97 mmol) and trimethylphosphite (5.0 mL, 5.26 g, 42 mmol) was heated at 110° C. for 3 h. The solvent was then removed under reduced pressure and the residue chromatographed using a 10-50% gradient of heptane/ethyl acetate to yield benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue chromatographed

Sources & evidence

ORD record
ord-cecf1de319e0493e9b23f4a396fdc1ce
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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