Trifluoroacetic acid → 4-Iodo-5-methylpyridin-2-amine

HRID 537030Notes

Reaction equation

HRID 537030 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:12]=[C:11]([I:13])[C:10]([CH3:14])=[CH:9][N:8]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:13][C:11]1[C:10]([CH3:14])=[CH:9][N:8]=[C:7]([NH2:6])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66747638N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine

Product 1

HCID 667478634-Iodo-5-methylpyridin-2-amineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (118 g, 310 mmol) in DCM (1900 mL) was added TFA (360 mL, 4830 mmol). The reaction mixture was allowed to stir at rt for 2 h and was then concentrated. The residue was dissolved in EtOAc and diluted with saturated aqueous NaHCO3. The mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give 4-iodo-5-methylpyridin-2-amine (53 g, 75%) which was used in the next step without purification.

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. additiondiluted with saturated aqueous NaHCO3
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-53c9cc6ca31e48b7a5fe269bf9f6357e
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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