Methyl iodide → HCID 67388013, compound

HRID 906498Notes

Reaction equation

HRID 906498 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3.[H-].[Na+].[CH3:27]I>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]([CH3:27])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67387962HCID 67387962, compound2×

Product 1

HCID 67388013HCID 67388013, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg of 3-(2,4-dimethylphenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one (compound 101) are dissolved in 10 ml of DMF. 31 mg of 95% NaH are added and the mixture is stirred at AT for 30 minutes. 380 μl of methyl iodide are added and the mixture is stirred at AT for 18 hours. It is evaporated to dryness. The residue is taken up in CH2Cl2 and the organic phase is washed with NaCl and then water, dried and evaporated. The residue is taken up in Et2O, filtration is carried out and drying is carried out. 300 mg of the expected product are obtained, M.p.=150° C.

Workup

  1. stirringthe mixture is stirred at AT for 18 hours
  2. customIt is evaporated to dryness
  3. washthe organic phase is washed with NaCl
  4. dry with materialwater, dried
  5. customevaporated
  6. filtrationfiltration
  7. customdrying

Sources & evidence

ORD record
ord-dac5a81cefe742a78bea638e94929cf2
Source dataset
uspto-grants-2011_09
Patent number
US08012991B2

Reaction notes

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