Trifluoroacetic acid → Methyl 6-amino-4-bromopyridine-2-carboxylate

HRID 421984Notes

Reaction equation

HRID 421984 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8]C(OC(C)(C)C)=O)[N:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:8][C:6]1[N:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25067269Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

Product 1

HCID 29919299Methyl 6-amino-4-bromopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7.23 g of methyl 4-bromo-6-t-butoxycarbonylamino-pyridine-2-carboxylate was dissolved in 30 ml of chloroform, and then 15 ml of trifluoroacetic acid was added thereto, followed by stirring at room temperature for 1 hour. After concentrating the reaction mixture, the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1) to give the title compound.

Workup

  1. concentrationAfter concentrating the reaction mixture
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-71ad255b3fb8445f8311c1c3009d6ff5
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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