methyl 3-hydroxy-5-iodobenzoate

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

Procedure: The compound of Production Example 133 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, (2R)-1-(tert-butyldimethylsiloxy)-2-hydroxypropane, 4-methanesulfonylbenzenethiol and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 133 was obtained as a colorless amorphous substance

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

Procedure: The compound of Production Example 133 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, (2R)-1-(tert-butyldimethylsiloxy)-2-hydroxypropane, 4-methanesulfonylbenzenethiol and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 133 was obtained as a colorless amorphous substance

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

Procedure: The compound of Production Example 124 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, 1-tert-dimethylsiloxy-2-hydroxypropane, 2-mercapto-[1,3,4]thiadiazole and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 124 was obtained as a colorless amorphous substance

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

Procedure: The compound of Production Example 124 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, 1-tert-dimethylsiloxy-2-hydroxypropane, 2-mercapto-[1,3,4]thiadiazole and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 124 was obtained as a colorless amorphous substance

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

Procedure: The compound of Production Example 124 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, 1-tert-dimethylsiloxy-2-hydroxypropane, 2-mercapto-[1,3,4]thiadiazole and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 124 was obtained as a colorless amorphous substance

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After adding 298 mg (2.16 mmol) of potassium carbonate and 0.12 ml (1.29 mmol) of 2-bromopropane to a solution of 120 mg (0.43 mol) of 3-hydroxy-5-iodobenzoic acid methyl ester in N,N-dimethylformamide (4.0 ml), the reaction mixture was stirred at 80° C. overnight. Water was added to the reaction mixture, extraction was performed with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1) to obtain 133 mg of 5-iodo-3-isopropoxybenzoic acid methyl ester (yield: 96%) as a colorless oil. the organic layer was washed with brine dried concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1)

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

Procedure: The compound of Production Example 133 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, (2R)-1-(tert-butyldimethylsiloxy)-2-hydroxypropane, 4-methanesulfonylbenzenethiol and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 133 was obtained as a colorless amorphous substance

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

Procedure: The compound of Production Example 124 was obtained as a colorless amorphous substance using 3-hydroxy-5-iodobenzoic acid methyl ester, 1-tert-dimethylsiloxy-2-hydroxypropane, 2-mercapto-[1,3,4]thiadiazole and 3-amino-1-methyl-1H-pyrazole, by the same method as in Production Example 74 or 82, a corresponding method, or a combination thereof with an ordinary method. The compound of Production Example 124 was obtained as a colorless amorphous substance

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After adding 298 mg (2.16 mmol) of potassium carbonate and 0.12 ml (1.29 mmol) of 2-bromopropane to a solution of 120 mg (0.43 mol) of 3-hydroxy-5-iodobenzoic acid methyl ester in N,N-dimethylformamide (4.0 ml), the reaction mixture was stirred at 80° C. overnight. Water was added to the reaction mixture, extraction was performed with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1) to obtain 133 mg of 5-iodo-3-isopropoxybenzoic acid methyl ester (yield: 96%) as a colorless oil. the organic layer was washed with brine dried concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1)