2-Cyclopenten-1-one → HCID 57701046, compound

HRID 1186297Notes

Reaction equation

HRID 1186297 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[C:13]1(=[O:18])[CH2:17][CH2:16][CH:15]=[CH:14]1>CC#N>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:15]1[CH2:16][CH2:17][C:13](=[O:18])[CH2:14]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 225235-Nitroindole

Product 1

HCID 57701046HCID 57701046, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-nitroindole (2.0 g, 12.80 mmol) in dry MeCN (10.0 mL) was added cyclopent-2-enone (2.0 mL, 23.87 mmol) and Bi(NO3)3 (0.06 g, 0.13 mmol) and the mixture stirred overnight at room temperature. The solvent then was evaporated and the crude was purified by column chromatography (50% Hexane: 50% EtOAc) to obtain the title compound (1.63 g, 52%) as a yellow solid. 1H-NMR (CDCl3) δ 2.05-2.18 (m, 1H), 2.37-2.48 (m, 3H), 2.54-2.66 (m, 1H), 2.80 (dd, 1H, J=7.2, 7.8 Hz), 3.72-3.82 (m, 1H), 7.15 (d, 1H, J=1.5 Hz), 7.42 (d, 1H, J=9.0 Hz), 8.15 (dd, 1H, J=2.4, 9.0 Hz), 8.39 (brs, 1H, NH), 8.62 (d, 1H, J=2.4 Hz); ESI-MS (m/z, %) 267 (MNa+, 100).

Workup

  1. customThe solvent then was evaporated
  2. customthe crude was purified by column chromatography (50% Hexane: 50% EtOAc)

Sources & evidence

ORD record
ord-c7f31842983f4600a2ece39b6e3dd71c
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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