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

HRID 1477272Notes

Reaction equation

HRID 1477272 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:10]=[N:11][C:12]([Cl:16])=[CH:13][C:14]=1[I:15])C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:16][C:12]1[N:11]=[CH:10][C:9]([NH:7][CH3:6])=[C:14]([I:15])[CH:13]=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-375a4e5a667e439bb5934451cf611187
Source dataset
uspto-grants-2016_08
Patent number
US09403772B2

Reaction notes

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