6-(2-methoxyethoxy)-1H-indole → benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate

HRID 2361393Notes

Reaction equation

HRID 2361393 reaction equation
[CH3:1][C:2]1[C:7](/[CH:8]=[C:9](/[N+:11]([O-:13])=[O:12])\[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[CH:35][NH:36]2)=[CH:32][CH:31]=1>C1COCC1>[CH3:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:38]=[C:37]2[C:33]([C:34]([CH:8]([C:7]3[C:2]([CH3:1])=[C:3]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:4]=[CH:5][CH:6]=3)[CH:9]([N+:11]([O-:13])=[O:12])[CH3:10])=[CH:35][NH:36]2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 679948936-(2-methoxyethoxy)-1H-indoleHCID 70651684(E)-benzyl 2-methyl-3-(2-nitroprop-1-enyl)phenylcarbamate

Product 1

HCID 67994587benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamateYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-Benzyl 2-methyl-3-(2-nitroprop-1-enyl)phenylcarbamate (0.6849 g, 1.574 mmol) and 6-(2-methoxyethoxy)-1H-indole (0.602 g, 3.15 mmol) were dissolved in THF (50 mL), concentrated in vacuo, and melted at 140° C. for 12 h. After cooling to room temperature, the crude product was purified by flash chromatography using an ISCO 40 g column (solid loading) eluting with 20-75% EtOAc/hexane. Appropriate fractions were collected and concentrated in vacuo to give benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate (0.4102 g, 0.793 mmol, 50.4% yield, mixture of 2 isomers) as a yellow oil, LC/MS (M+H)=518.12, 518.13.

Workup

  1. concentrationconcentrated in vacuo, and melted at 140° C. for 12 h
  2. customthe crude product was purified by flash chromatography
  3. washeluting with 20-75% EtOAc/hexane
  4. customAppropriate fractions were collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69f3986ebcac46c4bb56fb472ec52e42
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…