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

HRID 62927

Reaction equation

HRID 62927 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](=[O:30])[CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([OH:28])=[C:23]([F:29])[CH:22]=1)C>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:28][C:24]3[C:23]([F:29])=[CH:22][C:21]([CH2:20][CH2:19][C:18]([OH:30])=[O:17])=[CH:26][C:25]=3[F:27])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 742222833-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acidYield 79.4%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.037 g, 0.16 mmol) obtained in Step C of Preparation Example 8 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.037 g, 0.16 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 (0.050 g, 79%).

Workup

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

Sources & evidence

ORD record
ord-33536d66c0634b0cb25b93036fe09bb6
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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