6-(Tetrahydrofuran-3-yloxy)-1H-indole → Benzyl 2-methyl-3-(2-nitro-1-(6-(tetrahydrofuran-3-yloxy)-1H-indol-3-yl)ethyl)phenylcarbamate

HRID 2361299Notes

Reaction equation

HRID 2361299 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([O:6][C:7]2[CH:15]=[C:14]3[C:10]([CH:11]=[CH:12][NH:13]3)=[CH:9][CH:8]=2)[CH2:2]1.[CH3:16][C:17]1[C:22](/[CH:23]=[CH:24]/[N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[CH3:16][C:17]1[C:22]([CH:23]([C:11]2[C:10]3[C:14](=[CH:15][C:7]([O:6][CH:3]4[CH2:4][CH2:5][O:1][CH2:2]4)=[CH:8][CH:9]=3)[NH:13][CH:12]=2)[CH2:24][N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 679946796-(Tetrahydrofuran-3-yloxy)-1H-indoleHCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

Product 1

HCID 67994787Benzyl 2-methyl-3-(2-nitro-1-(6-(tetrahydrofuran-3-yloxy)-1H-indol-3-yl)ethyl)phenylcarbamateYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(Tetrahydrofuran-3-yloxy)-1H-indole (0.632 g, 3.11 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (0.800 g, 2.56 mmol) were dissolved in THF (50 mL). The solution was then concentrated under vacuum to dryness. The solid mixture was melted at 130° C. and heated at this temperature for 6 hr. The mixture was subjected to ISCO (120 g silica gel, solid loading, 25-65% ethyl acetate/hexane) to afford the desired product (0.612 g, 1.187 mmol, 46.3% yield) as a beige solid.

Workup

  1. concentrationThe solution was then concentrated under vacuum to dryness
  2. temperatureheated at this temperature for 6 hr

Sources & evidence

ORD record
ord-dc63134241b74c7d96f2811e55cf18d9
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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