Methyl iodide → HCID 68832709, compound

HRID 490568Notes

Reaction equation

HRID 490568 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[C:8](=[O:18])[NH:7]1.[H-].[Na+].I[CH3:26]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[C:8](=[O:18])[N:7]1[CH3:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68832721HCID 68832721, compound

Product 1

HCID 68832709HCID 68832709, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3,4-difluoro-benzyl)-5-nitro-1,2-dihydro-indazol-3-one (prepared in analogy to example 80 using 3,4-difluorobenzylbromide (step A)) (0.2 g) in DMF was added NaH (0.019 g) and the solution was stirred for 1 hour. Iodomethane (0.14 g) was then added and the mixture was stirred overnight. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo to afford a crude orange residue. Flash column chromatography of the crude residue over silica gel afforded the desired 1-(3,4-difluoro-benzyl)-2-methyl-5-nitro-1,2-dihydro-indazol-3-one (0.11 g) as a yellow solid. MS (ESI−): 318.1 ([M−H]−).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a crude orange residue

Sources & evidence

ORD record
ord-86177734ad0a472782eabb9bee6be1fa
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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