Methyl iodide → 2-chloro-N-(3-fluoro-4-nitro-phenyl)-N-methyl-pyridin-4-amine

HRID 2200107Notes

Reaction equation

HRID 2200107 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.CI.[C:21]([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH3:21])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 900206142-Chloro-N-(3-fluoro-4-nitrophenyl)-4-pyridinamine

Product 1

HCID 900204772-chloro-N-(3-fluoro-4-nitro-phenyl)-N-methyl-pyridin-4-amineYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add 2-chloro-N-(3-fluoro-4-nitro-phenyl)pyridin-4-amine (300 mg, 1.12 mmol), methyl iodide (174 mg, 1.23 mmol) and K2CO3 (201 mg, 1.45 mmol) in DMF (6 mL). Stir the reaction at 70° C. for 3 hrs. TLC (EtOAc:PE=1:1) shows the reaction is complete, cool the reaction to 0° C., add water, extract with EtOAc. Combine the organic layers. Wash with brine, dry over anhydrous Na2SO4. Concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (190 mg, 45%). MS: (M+1): 282.2.

Workup

  1. customthe reaction at 70° C. for 3 hrs
  2. temperaturecool
  3. customthe reaction to 0° C.
  4. extractionextract with EtOAc
  5. washWash with brine
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationConcentrate
  8. customto give the crude product
  9. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-55e8c8b8674f45baa7952608fe395ac5
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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