Methyl iodide → 3-Chloro-7-iodo-1-methyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one

HRID 1037395Notes

Reaction equation

HRID 1037395 reaction equation
[Cl:1][C:2]1[C:6]2=[CH:7][CH:8]=[C:9]3[C:14]([O:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([I:21])[C:10]3=[O:22])=[C:5]2[NH:4][N:3]=1.[C:23](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[C:6]2=[CH:7][CH:8]=[C:9]3[C:14]([O:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([I:21])[C:10]3=[O:22])=[C:5]2[N:4]([CH3:23])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178516689HCID 178516689, compound

Product 1

HCID 670679063-Chloro-7-iodo-1-methyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred ice-cooled solution of 3-chloro-7-iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one (42 mg, 0.10 mmol) in DMF (2 mL), was added cesium carbonate (65 mg, 0.2 mmol). After 5 min, iodomethane (0.0185 mL, 0.3 mmol) was added. After a further 5 min, the reaction mixture was allowed to warm to RT. After a further 15 min, the resulting mixture was partitioned between EtOAc and water. The resulting biphasic mixture was separated, the organic phase was further extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 30 to 50% EtOAc in cyclohexane) to afford the title compound as a white solid (25 mg, 58%), LCMS (Method H): RT=4.19 min, [M+H]+=437/439.

Workup

  1. waitAfter a further 5 min
  2. waitAfter a further 15 min
  3. customthe resulting mixture was partitioned between EtOAc and water
  4. customThe resulting biphasic mixture was separated
  5. extractionthe organic phase was further extracted with EtOAc
  6. washthe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa21e00f77f4479d9f4fb7fad1d4eab8
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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