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

HRID 1505862Notes

Reaction equation

HRID 1505862 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-84407de34f744beca8b2ce741f824db8
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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