Trifluoroacetic acid → 6-Chloro-4-iodopyridin-3-amine

HRID 1016636Notes

Reaction equation

HRID 1016636 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[C:11]([I:23])[CH:10]=1>ClCCl>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([NH2:15])=[C:11]([I:23])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 184070406-Chloro-4-iodopyridin-3-amineYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.4 mL) was added to a solution of 1,1-dimethylethyl (6-chloro-4-iodo-3-pyridinyl)carbamate (Description 7, 2.2 g, 6.2 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The mixture was washed with aqueous sodium hydroxide (1M), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (70:30), to give the title compound as a yellow solid (1.3 g, 82%). 1H NMR (360 MHz, CDCl3) δ 7.80 (1H, s), 7.60 (1H, s), and 4.13 (2H, br s). m/z (ES+) 255, 257 (M+1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe mixture was washed with aqueous sodium hydroxide (1M)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with isohexane/EtOAc (70:30)

Sources & evidence

ORD record
ord-5d95312582b840ecb02ba292f3443061
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

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