methyl 3-(3-fluoro-4-hydroxyphenyl)propanoate

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.032 g, 0.14 mmol) obtained in Step C of Preparation Example 8 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.045 g, 84%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 23 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.041 g, 82%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-propylsulfanyl-pyridine (0.030 g, 0.15 mmol) obtained in Step C of Preparation Example 14 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.031 g, 0.15 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.038 g, 73%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: (E)-3-(4-Benzyloxy-3-fluoro-phenyl)-acrylic acid methyl ester (0.37 g, 1.2 mmol) obtained in Step B was dissolved in EtOAc (4 mL) and MeOH (2 mL). The solution was added with 10% Pd/C (0.03 g), and the mixture was stirred under hydrogen atmosphere for 18 hours. The reactant was filtered by using celite, and the filtrate was washed with EtOAc to obtain the title compound (0.25 g, 98%). The reactant was filtered the filtrate was washed with EtOAc

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.032 g, 0.14 mmol) obtained in Step C of Preparation Example 8 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.045 g, 84%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 23 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.041 g, 82%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-propylsulfanyl-pyridine (0.030 g, 0.15 mmol) obtained in Step C of Preparation Example 14 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.031 g, 0.15 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.038 g, 73%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: (E)-3-(4-Benzyloxy-3-fluoro-phenyl)-acrylic acid methyl ester (0.37 g, 1.2 mmol) obtained in Step B was dissolved in EtOAc (4 mL) and MeOH (2 mL). The solution was added with 10% Pd/C (0.03 g), and the mixture was stirred under hydrogen atmosphere for 18 hours. The reactant was filtered by using celite, and the filtrate was washed with EtOAc to obtain the title compound (0.25 g, 98%). The reactant was filtered the filtrate was washed with EtOAc

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.032 g, 0.14 mmol) obtained in Step C of Preparation Example 8 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.045 g, 84%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 23 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.041 g, 82%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-propylsulfanyl-pyridine (0.030 g, 0.15 mmol) obtained in Step C of Preparation Example 14 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.031 g, 0.15 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.038 g, 73%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: (E)-3-(4-Benzyloxy-3-fluoro-phenyl)-acrylic acid methyl ester (0.37 g, 1.2 mmol) obtained in Step B was dissolved in EtOAc (4 mL) and MeOH (2 mL). The solution was added with 10% Pd/C (0.03 g), and the mixture was stirred under hydrogen atmosphere for 18 hours. The reactant was filtered by using celite, and the filtrate was washed with EtOAc to obtain the title compound (0.25 g, 98%). The reactant was filtered the filtrate was washed with EtOAc