methyl 6-bromo-2,3-difluorobenzoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.16 g, 35.4 mmol), methyl 6-bromo-2,3-difluorobenzoate (8.11 g, 32.3 mmol), copper acetate (II) (0.49 g, 2.7 mmol) and potassium carbonate (4.46 g, 323 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere, and the solution was allowed to cool to room temperature and poured into water. The solution was made weakly acidic by the addition of acetic acid, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (0.86 g, 8% yield). under reflux for 1 hour under an argon atmosphere was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-bromo-2,3-difluorobenzoic acid (7.66 g, 32.3 mmol), methyl iodide (10 mL, 160 mmol) and potassium carbonate (5.36 g, 38.8 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 1 hour. The solution was poured into water, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (8.11 g, 100% yield). was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-bromo-2,3-difluorobenzoic acid (7.66 g, 32.3 mmol), methyl iodide (10 mL, 160 mmol) and potassium carbonate (5.36 g, 38.8 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 1 hour. The solution was poured into water, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (8.11 g, 100% yield). was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 6-bromo-2,3-difluorobenzoic acid and conc. H2SO4 in MeOH was heated at reflux for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the residue was carefully added a satd. aq. NaHCO3 solution. The resulting mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was dried under high vacuum to afford the title compound. ESI MS (M+H) 251. at reflux for 18 h concentrated under reduced pressure To the residue was carefully added a satd The resulting mixture was extracted with CH2Cl2 The combined extracts were dried over anhydrous Na2SO4 filtered concentrated under reduced pressure The residue obtained was dried under high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 6-bromo-2,3-difluorobenzoic acid and conc. H2SO4 in MeOH was heated at reflux for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the residue was carefully added a satd. aq. NaHCO3 solution. The resulting mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was dried under high vacuum to afford the title compound. ESI MS (M+H) 251. at reflux for 18 h concentrated under reduced pressure To the residue was carefully added a satd The resulting mixture was extracted with CH2Cl2 The combined extracts were dried over anhydrous Na2SO4 filtered concentrated under reduced pressure The residue obtained was dried under high vacuum

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.16 g, 35.4 mmol), methyl 6-bromo-2,3-difluorobenzoate (8.11 g, 32.3 mmol), copper acetate (II) (0.49 g, 2.7 mmol) and potassium carbonate (4.46 g, 323 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere, and the solution was allowed to cool to room temperature and poured into water. The solution was made weakly acidic by the addition of acetic acid, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (0.86 g, 8% yield). under reflux for 1 hour under an argon atmosphere was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-bromo-2,3-difluorobenzoic acid (7.66 g, 32.3 mmol), methyl iodide (10 mL, 160 mmol) and potassium carbonate (5.36 g, 38.8 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 1 hour. The solution was poured into water, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (8.11 g, 100% yield). was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 6-bromo-2,3-difluorobenzoic acid and conc. H2SO4 in MeOH was heated at reflux for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the residue was carefully added a satd. aq. NaHCO3 solution. The resulting mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was dried under high vacuum to afford the title compound. ESI MS (M+H) 251. at reflux for 18 h concentrated under reduced pressure To the residue was carefully added a satd The resulting mixture was extracted with CH2Cl2 The combined extracts were dried over anhydrous Na2SO4 filtered concentrated under reduced pressure The residue obtained was dried under high vacuum