5-Nitroindole → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

HRID 2247271Notes

Reaction equation

HRID 2247271 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].[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C[O-].[Na+]>CO>[CH3:13][N:14]1[CH2:15][CH:16]=[C:17]([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)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 225235-NitroindoleHCID 740491-Methyl-4-piperidoneHCID 10942334Sodium Methoxide

Product 1

HCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Nitroindole (2.6 g) was dissolved in anhydrous MeOH (100 ml), followed by N-methyl-4-piperidone (5 g) and NaOMe powder (5 g). The mixture was heated to reflux under N2 overnight. The mixture was concentrated in vacuo. The crude was partitioned between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a yellow solid. This solid was washed with EtOAc (5 mL) and MeOH (2 ml) to afford the title compound as a bright yellow solid. MS:258 (M+1). Calc'd. for C14H15N3O2—257.29.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under N2 overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe crude was partitioned between saturated NaHCO3 solution and EtOAc
  5. dry with materialthe resulting organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow solid
  9. washThis solid was washed with EtOAc (5 mL) and MeOH (2 ml)

Sources & evidence

ORD record
ord-a570ce0820e946a79387b510946201c5
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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