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

HRID 62976Notes

Reaction equation

HRID 62976 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:17][C:18]([CH:20]1[CH2:22][CH:21]1[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([Cl:30])[CH:24]=1)=[O:19])C>>[Cl:30][C:25]1[CH:24]=[C:23]([CH:21]2[CH2:22][CH:20]2[C:18]([OH:19])=[O:17])[CH:28]=[CH:27][C:26]=1[O:29][CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][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 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 742229742-[3-Chloro-4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 75%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (49 mg, 0.23 mmol) obtained in Step C of Preparation Example 8 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (62 mg, 0.25 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 (65 mg, 75%).

Workup

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

Sources & evidence

ORD record
ord-8859b14694be467ea393d399bb5d09e0
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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