Sodium hydride → 2-(4-Allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethanol

HRID 576525Notes

Reaction equation

HRID 576525 reaction equation
[CH2:1]([C:4]1([CH3:19])[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:18])[CH2:5]1)[CH:2]=[CH2:3].[H-].[Na+].[O:22]1[CH2:24][CH:23]1[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:1]([C:4]1([CH3:19])[C:9]2[N:10]([CH2:24][CH:23]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[OH:22])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:18])[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109534834-(Oxiran-2-yl)pyridineHCID 673559434-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 673565382-(4-Allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethanolYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.5 g, 9.8 mmol) was dissolved in 18 mL of DMF and stirred for 10 min at RT. Sodium hydride (1.17 g, 29.2 mmol) was added portionwise and stiffing was continued for additional 10 min. This was followed by dropwise addition of 4-oxiranyl-pyridine (2.38 g, 19.6 mmol) as a solution in DMF. The reaction mixture was stirred at RT for 16 h, quenched with ice water and extracted with EtOAc (3×120 mL). The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized in ether to obtain 1 g of 2-(4-allyl-2,4,8-trimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethanol.

Workup

  1. waitstiffing was continued for additional 10 min
  2. stirringThe reaction mixture was stirred at RT for 16 h
  3. customquenched with ice water
  4. extractionextracted with EtOAc (3×120 mL)
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized in ether

Sources & evidence

ORD record
ord-d29cb0bee3244c85ad130cba524bd2d3
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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