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

HRID 62981Notes

Reaction equation

HRID 62981 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH2:10][CH2:11][CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:15][C:16]([CH:18]1[CH2:20][CH:19]1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([Cl:28])[CH:22]=1)=[O:17])C>>[Cl:28][C:23]1[CH:22]=[C:21]([CH:19]2[CH2:20][CH:18]2[C:16]([OH:17])=[O:15])[CH:26]=[CH:25][C:24]=1[O:27][CH2:2][C:3]1[C:4]([S:9][CH2:10][CH2:11][CH3:12])=[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 901182823-Chloromethyl-2-propylsulfanyl-pyridine

Product 1

HCID 742216672-[3-Chloro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 73%

Procedure

3-Chloromethyl-2-propylsulfanyl-pyridine (47 mg, 0.23 mmol) obtained in Step C of Preparation Example 14 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (61 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 (60 mg, 73%).

Workup

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

Sources & evidence

ORD record
ord-4c0fcb3f9bc143818e0a54298fb2179b
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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