Methanol → Methyl 3-amino-5-bromothiophene-2-carboxylate

HRID 2364013Notes

Reaction equation

HRID 2364013 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11]C(=O)C(F)(F)F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[NH2:11][C:4]1[CH:3]=[C:2]([Br:1])[S:6][C:5]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (5.30 g, 16.0 mmol), potassium carbonate (10.2 g, 70.4 mmol), MeOH (100 mL) and water (25 mL) was stirred at room temperature for 2 h. After removal of the solvent at reduced pressure, the residue was extracted with EtOAc, and the extract was washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 10:90 hexane /EtOAc) to give the title compound (3.32 g, 88%) as a yellow solid:

Workup

  1. customAfter removal of the solvent at reduced pressure
  2. extractionthe residue was extracted with EtOAc
  3. washthe extract was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent at reduced pressure
  7. customthe residue was purified by column chromatography (Purif, silica gel, hexane to 10:90 hexane /EtOAc)

Sources & evidence

ORD record
ord-a1effcd5f5a14069aa805e91cfeb8dc1
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…