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

HRID 1888557Notes

Reaction equation

HRID 1888557 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([F:15])=[CH:12][C:13]=1[I:14])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:15][C:11]1[N:10]=[CH:9][C:8]([NH2:7])=[C:13]([I:14])[CH:12]=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

(6-Fluoro-4-iodopyridin-3-yl)-carbamic acid tert-butyl ester (1.75 g, 5.18 mmol) was dissolved in DCM (25 mL) and TFA (5 mL) added. The mixture was stirred at ambient temperature for 1 h and then evaporated in vacuo. The resultant residue was treated with saturated aqueous sodium hydrogen carbonate solution (25 mL), diluted with water (100 mL) and extracted into ethyl acetate (2×100 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title compound as an orange oil, which crystallized on standing (1.23 g, 99%). 1H NMR (CDCl3, 300 MHz): 7.61 (d, J=1.6 Hz, 1H), 7.28-7.25 (m, 1H), 3.99 (s, 2H). LCMS (Method B): RT=2.52 min, M+H+=239.

Workup

  1. customevaporated in vacuo
  2. additionThe resultant residue was treated with saturated aqueous sodium hydrogen carbonate solution (25 mL)
  3. additiondiluted with water (100 mL)
  4. extractionextracted into ethyl acetate (2×100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1de3d6ef8d844e4fb76bdaa80a32cdd6
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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