Water → HCID 19799240, compound

HRID 2081202Notes

Reaction equation

HRID 2081202 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:7]=3[C:6]=2[CH:5]=1.[CH3:18]I.O>CN(C=O)C>[F:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:18])[C:8]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:7]=3[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19799247HCID 19799247, compound

Product 1

HCID 19799240HCID 19799240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil; 196 mg) was added to a stirred solution of 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (500 mg) in dry DMF (20 ml) at 21° under nitrogen. After 15 min, the solution was cooled (0°) and a 10% (v/v) solution of methyl iodide in DMF (1.6 ml) was added dropwise. After 10 min, water (150 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (3×50 ml), then brine (100 ml) and evaporated to give a solid which was purified by FCC Eluting with dichloromethane:methanol (80:1) to give the title compound (240 mg), m.p. 200°-202°.

Workup

  1. temperaturethe solution was cooled (0°)
  2. waitAfter 10 min
  3. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  4. washThe combined organic extracts were washed with water (3×50 ml)
  5. custombrine (100 ml) and evaporated
  6. customto give a solid which
  7. customwas purified by FCC
  8. washEluting with dichloromethane:methanol (80:1)

Sources & evidence

ORD record
ord-9270dc58495541b4b6ed140e45b650d8
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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