Potassium Hydroxide → (E)-2-methyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400418Notes

Reaction equation

HRID 1400418 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]([CH2:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)(O)[CH3:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[OH-].[K+]>S(Cl)(Cl)=O>[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6](/[CH:13]=[C:14](/[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)\[CH3:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 497795901-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol

Product 1

HCID 59454924(E)-2-methyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

1-(1,2,3,4-Tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-2-(pyridin-4-yl)propan-2-ol (600 mg, 1.86 mmol) was dissolved in thionyl chloride (8 mL) and the solution was stirred for 1 h. Excess thionyl chloride was removed under reduced pressure and the residue was dissolved in N-methyl-2-pyrrolidone (3 mL) and the solution was stirred for 5 min. at RT. Powdered KOH (690 mg, 12.32 mmol) was added and the reaction mixture was heated at 100° C. for 1-2 h. The reaction mixture was cooled to RT, diluted with ice water and extracted with EtOAc. The organic layer washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 2% MeOH-DCM. 1H NMR (CD3OD, HCl salt) δ (ppm): 8.85 (d, 2H), 8.40 (d, 2H), 7.82 (d, 1H), 7.60 (d, 1H), 7.30 (m, 2H), 7.20 (m, 1H), 4.80 (d, 1H), 4.40 (d, 1H), 3.90 (m, 1H), 3.60 (m, 2H), 3.20 (m, 1H), 3.10 (s, 3H), 2.20 (s, 3H).

Workup

  1. customExcess thionyl chloride was removed under reduced pressure
  2. dissolutionthe residue was dissolved in N-methyl-2-pyrrolidone (3 mL)
  3. stirringthe solution was stirred for 5 min. at RT
  4. temperatureThe reaction mixture was cooled to RT
  5. extractionextracted with EtOAc
  6. washThe organic layer washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 2% MeOH-DCM

Sources & evidence

ORD record
ord-82d37980c7c54a54948ab9f52d2470c6
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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