2-Chloro-4-fluoro-5-methylaniline

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at −65° C. with a solution of butylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at −65° C. for 10 min, treated at −65° C. with a solution of methylthioacetone (1.080 g) in methylene chloride (5 ml) stirred at −65° C. for 1 hour, treated at −65° C. with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g). stirred at −65° C. for 1 hour to reach ambient temperature The solution was washed dried (MgSO4) evaporated The residue was purified by silica chromatography

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

Procedure: The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-chloro-4-fluoro-5-methylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.

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

Procedure: The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-chloro-4-fluoro-5-methylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.

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

Procedure: The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-chloro-4-fluoro-5-methylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at −65° C. with a solution of butylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at −65° C. for 10 min, treated at −65° C. with a solution of methylthioacetone (1.080 g) in methylene chloride (5 ml) stirred at −65° C. for 1 hour, treated at −65° C. with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g). stirred at −65° C. for 1 hour to reach ambient temperature The solution was washed dried (MgSO4) evaporated The residue was purified by silica chromatography

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at −65° C. with a solution of butylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at −65° C. for 10 min, treated at −65° C. with a solution of methylthioacetone (1.080 g) in methylene chloride (5 ml) stirred at −65° C. for 1 hour, treated at −65° C. with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g). stirred at −65° C. for 1 hour to reach ambient temperature The solution was washed dried (MgSO4) evaporated The residue was purified by silica chromatography

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

Procedure: Using ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (4.35 g, 21.0 mmol) and 2-chloro-4-fluoro-5-methylaniline (3.02 g, 18.9 mmol) instead of 4-fluoro-2-methylaniline, and in the same manner as in Example 1 step 1, the title compound (5.54 g, 76%) was obtained.

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

Procedure: The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-chloro-4-fluoro-5-methylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.

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

Procedure: The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-chloro-4-fluoro-5-methylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at −65° C. with a solution of butylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at −65° C. for 10 min, treated at −65° C. with a solution of methylthioacetone (1.080 g) in methylene chloride (5 ml) stirred at −65° C. for 1 hour, treated at −65° C. with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g). stirred at −65° C. for 1 hour to reach ambient temperature The solution was washed dried (MgSO4) evaporated The residue was purified by silica chromatography