Sodium hydride → 3-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-one

HRID 517851Notes

Reaction equation

HRID 517851 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1.Br[CH:19]1[CH2:23][CH2:22][N:21]([CH3:24])[C:20]1=[O:25]>CN(C=O)C>[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[N:8]([CH:19]3[CH2:23][CH2:22][N:21]([CH3:24])[C:20]3=[O:25])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 111829543-Bromo-1-methylpyrrolidin-2-one

Product 1

HCID 441601853-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-oneYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (36 mg, 1.5 mmol) and 2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) in DMF (5 mL) was stirred at 0° C. 3-bromo-1-methylpyrrolidin-2-one (176 mg, 1.0 mmol) in DMF (3 mL) was added dropwise to the reaction mixture which was stirred at RT for 12 hours. After completion of the reaction, the reaction mixture was quenched with ice cold water and the product extracted with Ethyl Acetate. The organic layer isolated was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography to obtain 20 mg of 3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-one. 1H NMR (CDCl3) FREEBASE 7.10 (s, 1H), 7.05 (d, 1H), 6.92 (d, 1H), 5.05 (m, 1H), 4.80 (m, 1H), 3.80 (m, 1H), 3.50 (m, 2H), 3.40 (m, 1H), 3.20 (m, 3H), 3.0 (s, 3H), 2.80 (s, 3H), 2.40 (s, 3H), 2.20 (m, 2H).

Workup

  1. stirringwas stirred at RT for 12 hours
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with ice cold water
  4. extractionthe product extracted with Ethyl Acetate
  5. customThe organic layer isolated
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe crude obtained
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-da830b056f0f47f696e672e760926316
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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