Water → 6-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indole

HRID 2081221Notes

Reaction equation

HRID 2081221 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][NH:21][C:22]=4[CH3:23])[C:15](=O)[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][NH:21][C:22]=4[CH3:23])[CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 172999LurosetronHCID 21226445Aluminium lithium hydride

Product 1

HCID 197992756-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indoleYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl -1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (277 mg) in dry THF (75 ml) was treated portionwise with lithium aluminium hydride (67 mg) under nitrogen, and the suspension was then heated at reflux for 2 h. After cooling, water (10 ml) was added dropwise followed by sodium sulphate, and the mixture was then filtered. The filtrate was adsorbed onto silica and purified by FCC eluting with System A (100:8:1) to give the title compound (196 mg) as a solid, m.p. 188.5°-189.5°.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was then filtered
  5. custompurified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-324944ccacea4e949ac9f51a8b5bbf63
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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