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

HRID 557366Notes

Reaction equation

HRID 557366 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-c9c41575ae424e7492f15f947389169d
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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