Water → 6-Fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

HRID 2081201Notes

Reaction equation

HRID 2081201 reaction equation
[H-].[Na+].[F:3][C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:18]I.O>CN(C=O)C>[F:3][C:4]1[C:12]2[N:11]([CH3:18])[C:10]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 157124986-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 157125046-Fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil; 196 mg) was added to a stirred suspension of 6-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (500 mg) in dry DMF (10 ml) under nitrogen. After 30 min the solution was cooled (0°), and methyl iodide (0.153 ml) was added. After stirring for 15 min the suspension was poured into water 950 ml) and extracted with dichloromethane (3×25 ml). The combined, dried organic extracts were evaporated to give a solid (ca. 530 mg) which was purified by FCC eluting with System A (250:10:1) to give the title compound (130 mg), m.p. 242°.

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane (3×25 ml)
  3. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-895920e9010d4854afce918fbf7fa93a
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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