Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-[4-(6-Sec-butylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid

HRID 62938Notes

Reaction equation

HRID 62938 reaction equation
[CH:1]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12]Cl)[N:7]=1)([CH2:3][CH3:4])[CH3:2].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:1]([S:5][C:6]1[N:7]=[C:8]([CH2:12][O:27][C:23]2[C:22]([F:28])=[CH:21][C:20]([CH2:19][CH2:18][C:17]([OH:29])=[O:16])=[CH:25][C:24]=2[F:26])[CH:9]=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90117937HCID 90117937, compound

Product 1

HCID 742225283-[4-(6-Sec-butylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-propionic acidYield 65%

Procedure

2-sec-Butylsulfanyl-6-chloromethyl-pyridine (0.06 g, 0.27 mmol) obtained in Step C of Preparation Example 5 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester obtained in Step D of Preparation Example 2 were used to react in the same manner as in Step A Example 1 to obtain the title compound (0.074 g, 65%).

Workup

  1. customto react in the same manner as in Step A Example 1

Sources & evidence

ORD record
ord-81a336312cef4b7cbbd29f5410df9866
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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