Methyl iodide → HCID 9994544, compound

HRID 847509Notes

Reaction equation

HRID 847509 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[C:20](=[O:21])[N:11]3[C:12]4[C:17]([C:18]([CH3:19])=[C:10]3[CH2:9][CH2:8]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:3]=[CH:2]1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]2[C:20](=[O:21])[CH:7]([CH2:6][C:4]3[N:3]=[CH:2][N:1]([CH3:24])[CH:5]=3)[CH2:8][CH2:9][C:10]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178421668HCID 178421668, compound

Product 1

HCID 9994544HCID 9994544, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 8,9-dihydro-7-[(1H-imidazol-4-yl)-methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (1.4 g) in N,N-dimethylformamide (14 ml) at 5° C. was added sodium hydride (60% in mineral oil) (220 mg). After stirring for 1 hour at 5° C, methyl iodide (852 mg) in dimethylformamide (5 ml) was added dropwise at 5° C. for 10 minutes. The mixture was stirred at 5° C. for 1 hour and at 20° C. for 2 hours. After evaporation of the solvent, the residue was diluted with 5% methanol-chloroform. The organic layer was washed twice with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The obtained residue contained two products which showed close Rf values (0.5 and 0.4 respectively) by TLC (20% methanol-chloroform). Separation with silica gel column chromatography (5% methanol-chloroform) gave two fractions. The first eluted fraction, containing a mixture of two products, was concentrated. The crystalline residue was recrystallized from ethyl acetate to give 8,9-dihydro-10-methyl-7-[(1-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (0.4 g).

Workup

  1. stirringThe mixture was stirred at 5° C. for 1 hour and at 20° C. for 2 hours
  2. customAfter evaporation of the solvent
  3. additionthe residue was diluted with 5% methanol-chloroform
  4. washThe organic layer was washed twice with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customshowed close Rf values (0.5 and 0.4 respectively) by TLC (20% methanol-chloroform)
  8. customSeparation with silica gel column chromatography (5% methanol-chloroform)
  9. customgave two fractions
  10. additionThe first eluted fraction, containing
  11. additiona mixture of two products
  12. concentrationwas concentrated
  13. customThe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e9e9159024194cd6837c5d1018769482
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

Loading…