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

HRID 1888399Notes

Reaction equation

HRID 1888399 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[I:14])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl: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 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 184070406-Chloro-4-iodopyridin-3-amineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (3.67 g, 10.3 mmol) was dissolved in DCM (32 mL) and TFA (8 mL) was added. The reaction mixture was stirred at ambient temperature for 2 h and then evaporated in vacuo. The resultant residue was treated with 5N aqueous sodium hydroxide solution (25 mL), diluted with water (100 mL) and extracted into ethyl acetate (2×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as yellow solid (2.37 g, 90%). 1H NMR (CD3OD, 300 MHz): 7.80 (s, 1H), 7.60 (s, 1H), 4.14 (s, 2H). LCMS (Method B): RT=3.00 min, M+H+=255.

Workup

  1. customevaporated in vacuo
  2. additionThe resultant residue was treated with 5N aqueous sodium hydroxide solution (25 mL)
  3. additiondiluted with water (100 mL)
  4. extractionextracted into ethyl acetate (2×100 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f50c69725484463b917e125ecd76d0e8
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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