Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid

HRID 62935Notes

Reaction equation

HRID 62935 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](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([OH:27])=[C:22]([F:28])[CH:21]=1)C>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:27][C:23]3[C:22]([F:28])=[CH:21][C:20]([CH2:19][CH2:18][C:17]([OH:29])=[O:16])=[CH:25][C:24]=3[F:26])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridine

Product 1

HCID 742224403-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acidYield 82%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.113 mmol) obtained in Step C of Preparation Example 23 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (26 mg, 0.113 mmol) obtained in Step D of Preparation Example 2 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (35 mg, 82%).

Workup

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

Sources & evidence

ORD record
ord-024881e5585443eda5012393d6d6eb26
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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