5-Nitroindole → (4-(5-Nitro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)(phenyl)methanone

HRID 552934Notes

Reaction equation

HRID 552934 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].N1CCCC1.[C:18]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:29]1[CH2:30][CH2:31][N:26]([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:25])[CH2:27][CH:28]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 225235-NitroindoleHCID 31268PyrrolidineHCID 90583N-Benzoyl-4-piperidone

Product 1

HCID 57474456(4-(5-Nitro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)(phenyl)methanoneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-nitroindole (38) (0.5 g, 3.083 mmol) in dry ethanol (15 mL) was treated with pyrrolidine (0.77 mL, 9.250 mmol), 1-benzoyl-4-piperidone (1.0 g, 4.933 mmol) at room temperature and resulting solution was refluxed for 3 days. The reaction cooled to room temperature and the solid was filtered off. The product was washed with cold ethanol (2×10 mL) and dried under vacuum to obtain compound 68 (1.05 g, 98%) as a solid. mp 280-282° C.; 1H NMR (DMSO-d6) δ 2.55-2.61 (m, 2H), 3.54-3.58 (m, 1H), 3.86-3.90 (m, 1H), 4.15-4.34 (m, 2H), 6.14-6.30 (m, 1H), 7.39-7.55 (m, 5H), 7.67 (d, 1H, J=9.6 Hz), 7.72 (s, 1H), 8.03 (d, 1H, J=8.1 Hz), 8.70-8.78 (m, 1H), 11.94 (s, 1H); ESI-MS m/z (%): 348 (M+, 100), 276 (83), 244 (40).

Workup

  1. customresulting solution
  2. temperaturewas refluxed for 3 days
  3. filtrationthe solid was filtered off
  4. washThe product was washed with cold ethanol (2×10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-85b8b5608aa646378de769211336cba7
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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