2-(3-Chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester → 2-[3-Chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid

HRID 62977Notes

Reaction equation

HRID 62977 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:16][C:17]([CH:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([Cl:29])[CH:23]=1)=[O:18])C>>[Cl:29][C:24]1[CH:23]=[C:22]([CH:20]2[CH2:21][CH:19]2[C:17]([OH:18])=[O:16])[CH:27]=[CH:26][C:25]=1[O:28][CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 901181992-(3-Chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl esterHCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridine

Product 1

HCID 742217612-[3-Chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 84%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (52 mg, 0.26 mmol) obtained in Step C of Preparation Example 23 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (70 mg, 0.29 mmol) obtained in Step B of Preparation Example 47 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (77 mg, 84%).

Workup

  1. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-efca8579914745b6ad94e529d4e06f47
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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