Methyl iodide → HCID 67173014, compound

HRID 551092Notes

Reaction equation

HRID 551092 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:14][C:13](=[O:15])[CH:6]3[CH2:7][C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[H-].[Na+].I[CH3:19]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[NH:14][C:13](=[O:15])[C:6]3([CH3:19])[CH2:7][C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67174143HCID 67174143, compound

Product 1

HCID 67173014HCID 67173014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (±)-7-fluoro-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione from Step E (608 mg, 2.95 mmol) in degassed DMF (10 mL) at 0° C. was added sodium hydride (142 mg of a 60% dispersion in mineral oil, 3.54 mmol). The mixture was stirred for 15 min, then iodomethane (0.184 mL, 2.95 mmol) was added and stirring was continued for 1 h. The reaction mixture was poured onto H2O (100 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with H2O (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=221 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. additionThe reaction mixture was poured onto H2O (100 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organic extracts were washed with H2O (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-f1f53a81c18b4ebf8128da79cad31f23
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…