5-Nitroindole → HCID 57474453, compound

HRID 1186269Notes

Reaction equation

HRID 1186269 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].[CH2:13]([N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)[CH3:14].N1CCCC1>CO.O>[CH2:13]([N:15]1[CH2:16][CH:17]=[C:18]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=2)[CH2:19][CH2:20]1)[CH3:14]

Participants

6

Reactant 3

HCID 225235-NitroindoleHCID 31268PyrrolidineHCID 771591-Ethylpiperidin-4-one

Product 1

HCID 57474453HCID 57474453, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-nitro-1H-indole (0.67 g, 4.13 mmol), 1-ethylpiperidin-4-one (1.094 mL, 8.26 mmol) and pyrrolidine (1.025 mL, 12.40 mmol) in dry methanol (10 mL) was refluxed for 48 h. The reaction was brought to room temperature, diluted with water and product was extracted into CH2Cl2 (2×50 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated, crude was stirred with isopropanol: hexanes, (15 mL, 1:7) and the yellow precipitate was filtered and dried to obtain 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (0.87 g, 78%). 1H NMR (DMSO-d6) δ 11.87 (s, 1H), 8.69 (d, 1H, J=2.1 Hz), 8.01 (dd, 1H, J=2.4, 9.0 Hz), 7.65 (s, 1H), 7.55 (d, 1H, J=9.0 Hz), 6.18 (s, 1H), 3.16-3.12 (m, 2H), 2.64 (t, 2H, J=5.1 Hz), 2.54-2.42 (m, 4H, merged with DMSO-peak), 1.70 (t, 3H, J=7.2 Hz); ESI-MS (m/z, %): 272 (MH+, 100).

Workup

  1. customwas brought to room temperature
  2. extractionwas extracted into CH2Cl2 (2×50 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. filtrationhexanes, (15 mL, 1:7) and the yellow precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-70b2f452d43d496bac91b7d769e8c327
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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