5-Nitroindole → HCID 57474453, compound

HRID 552930Notes

Reaction equation

HRID 552930 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.[CH2:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)[CH3:19]>C(O)C>[CH2:18]([N:20]1[CH2:21][CH:22]=[C:23]([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)[CH2:24][CH2:25]1)[CH3:19]

Participants

5

Reactant 3

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

Product 1

HCID 57474453HCID 57474453, compoundYield 42%

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 (0.65 mL, 9.250 mmol), N-ethyl-4-piperidone (0.8 mL, 6.167 mmol) at room temperature and the resulting solution was refluxed for 3 days. The reaction was brought to room temperature and solvent was evaporated. The crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95), and washed with ether (3×10 mL) to obtain compound 60 (0.35 g, 42%) as a solid. mp 188-190° C.; 1H NMR (DMSO-d6) δ: 1.07 (t, 3H, J=7.2 Hz), 2.41-2.50 (m, 4H), 2.63 (t, 2H, J=5.1 Hz), 3.10-3.15 (m, 2H), 6.18 (s, 1H), 7.55 (d, 1H, J=9.0 Hz), 7.65 (s, 1H), 8.01 (dd, 1H, J=2.1, 9.0 Hz), 8.69 (d, 1H, J=2.1 Hz), 11.86 (s, 1H)— ESI-MS m/z (%): 272 (M+, 100).

Workup

  1. temperaturethe resulting solution was refluxed for 3 days
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. customThe crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95)
  5. washwashed with ether (3×10 mL)

Sources & evidence

ORD record
ord-13ea9f4c0f604e6b8102638f0fb5452b
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

Loading…