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

HRID 1022896Notes

Reaction equation

HRID 1022896 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 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (5.3 g), potassium carbonate (10 g), methanol (100 mL) and water (25 mL) was stirred at room temperature for 2 hr. The reaction system was concentrated under reduced pressure, and ethyl acetate and water were poured thereinto. The mixture was extracted with ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.3 g) as a yellow solid.

Workup

  1. concentrationThe reaction system was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere poured
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customInsoluble material was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a4fd534009c345238e0c1f0e2aa6f05e
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

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