Trifluoroacetic acid → HCID 58266485, compound

HRID 1888395Notes

Reaction equation

HRID 1888395 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([Br:15])=[CH:12][C:13]=1[I:14])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br: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 58266331tert-Butyl (6-bromo-4-iodopyridin-3-yl)carbamate

Product 1

HCID 58266485HCID 58266485, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Bromo-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (13.6 g, 34.1 mmol) was dissolved in dichloromethane (150 mL) and trifluoroacetic acid (50 mL) was then added. The resultant solution was stirred at ambient temperature for 2 h then evaporated under reduced pressure. The resultant residue was treated with a saturated solution of sodium hydrogen carbonate and the resultant solid was treated with water (50 mL) then extracted with ethyl acetate (2×200 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford the title compound as an off-white solid (10.0 g, 98%). 1H NMR (CDCl3, 300 MHz): 7.81 (s, 1H), 7.73 (s, 1H), 4.14 (s, 2H). LCMS (Method B): RT=3.03 min, M+H+=299/301.

Workup

  1. customthen evaporated under reduced pressure
  2. additionThe resultant residue was treated with a saturated solution of sodium hydrogen carbonate
  3. additionthe resultant solid was treated with water (50 mL)
  4. extractionthen extracted with ethyl acetate (2×200 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c61cb9155ff340ff838dfc7d11273f4f
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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