Trifluoroacetic acid → 6-Chloro-4-iodo-N-methylpyridin-3-amine

HRID 340424Notes

Reaction equation

HRID 340424 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8](C)[C:9](=O)OC(C)(C)C)=[C:4]([I:17])[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([I:17])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57443399Tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate

Product 1

HCID 574434006-Chloro-4-iodo-N-methylpyridin-3-amineYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate (62.5 g, 0.172 mol) in 500 mL of anhydrous DCM was added 180 mL of TFA. Then the solution was stirred at room temperature for 4 hrs. Concentrated to remove the solvent, and purified by flash chromatography to afford 45.1 g 6-chloro-4-iodo-N-methylpyridin-3-amine as a yellow solid (Yield: 97.3%).

Workup

  1. concentrationConcentrated
  2. customto remove the solvent
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b2a4e43e580642f4b91b3a107698e91e
Source dataset
uspto-grants-2014_11
Patent number
US08895586B2

Reaction notes

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