6-(2-methoxyethoxy)-1H-indole → Benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

HRID 2361271Notes

Reaction equation

HRID 2361271 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[CH3:15][C:16]1[C:21](/[CH:22]=[CH:23]/[N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:22]([C:21]3[C:16]([CH3:15])=[C:17]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=[CH:19][CH:20]=3)[CH2:23][N+:24]([O-:26])=[O:25])=[CH:11][NH:12]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 679948936-(2-methoxyethoxy)-1H-indoleHCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

Product 1

HCID 67994685Benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamateYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(2-Methoxyethoxy)-1H-indole (1.461 g, 88% purity, 6.72 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (1.75 g, 5.60 mmol) were dissolved in THF (50 mL). The solution was then concentrated under vacuum to dryness. The solid mixture was melted at 125° C. and heated at this temperature for 16 hr. The mixture was subjected to ISCO (220 g silica gel, solid loading, 25-65% ethyl acetate/hexane) to afford the desired product (1.75 g, 3.48 mmol, 62% yield) as a beige solid.

Workup

  1. concentrationThe solution was then concentrated under vacuum to dryness
  2. temperatureheated at this temperature for 16 hr

Sources & evidence

ORD record
ord-ea07ac6f69e64cb2bf89c62d2cd4a7a5
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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