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

HRID 887578Notes

Reaction equation

HRID 887578 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 100 mL anhydrous MeOH, followed by 5 g N-methyl-4-piperidone and NaOMe (5 g) powder. The mixture was heated to reflux under N2 overnight. The mixture was concentrated in vacuo, and was extracted 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 5 mL EtOAc and 2 mL MeOH to afford 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. extractionwas extracted 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 5 mL EtOAc and 2 mL MeOH
  10. customto afford a bright yellow solid

Sources & evidence

ORD record
ord-666fb850d1c3449b8900c8a01d1c5855
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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