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

HRID 1640907Notes

Reaction equation

HRID 1640907 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([I:16])[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([I:16])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66738095(6-Fluoro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 582666416-Fluoro-4-iodopyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tert-butyl 6-fluoro-4-iodopyridin-3-ylcarbamate (1.47 g, 4.35 mmol) in DCM (20 mL). Add trifluoroacetic acid (TFA) (20 mL). Stir at RT under N2 for 2 h. Remove the solvent under reduced pressure. Dry in vacuo to afford 6-fluoro-4-iodopyridin-3-amine in TFA salt (1.02 g, 99%) with 100% HPLC purity. MS (ES) m/z 239 [M+1]+.

Workup

  1. customRemove the solvent under reduced pressure
  2. customDry in vacuo

Sources & evidence

ORD record
ord-7d6d42959755413888c1db4b09f02e88
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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