(6-Methoxy-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester → 4-Iodo-6-methoxypyridin-3-amine

HRID 1506025Notes

Reaction equation

HRID 1506025 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=1[I:14])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:16][O:15][C:11]1[N:10]=[CH:9][C:8]([NH2:7])=[C:13]([I:14])[CH:12]=1

Participants

4

Reactant 1

HCID 58266614(6-Methoxy-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 110212874-Iodo-6-methoxypyridin-3-amineYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (6-methoxy-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (18 g, 51 mmol) in DCM (50 mL) and TFA (50 mL) 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 a brown foam (10 g, 60%).

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-0198eecc313d4e1c867ea5a3bcab56de
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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