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

HRID 1951655Notes

Reaction equation

HRID 1951655 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.FC(F)(F)C(O)=O>ClCCl>[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 115.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.65 g (19.6 mmol) (6-chloro-4-iodo-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester in 20 ml dichloromethane were added 20.0 ml (261 mmol) trifluoroacetic acid at 0° C. After stirring for 2 h at room temperature the reaction mixture was concentrated in vacuo. The residue was treated with 50 ml saturated sodium carbonate solution and extracted three times with 75 ml ethyl acetate. The combined organic layers were washed with 50 ml brine, dried over sodium sulfate and concentrated in vacuo to give 6.1 g (87%) of the title compound as a light brown solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was treated with 50 ml saturated sodium carbonate solution
  3. extractionextracted three times with 75 ml ethyl acetate
  4. washThe combined organic layers were washed with 50 ml brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f026505fd3045209b7672398189f8ff
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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