3-Chloromethyl-2-phenylsulfanyl-pyridine → 3-[3,5-Difluoro-4-(2-phenylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid

HRID 62929

Reaction equation

HRID 62929 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:18][C:19](=[O:31])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([OH:29])=[C:24]([F:30])[CH:23]=1)C>>[F:28][C:26]1[CH:27]=[C:22]([CH2:21][CH2:20][C:19]([OH:31])=[O:18])[CH:23]=[C:24]([F:30])[C:25]=1[O:29][CH2:2][C:3]1[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 192618653-Chloromethyl-2-phenylsulfanyl-pyridineHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

Product 1

HCID 742222863-[3,5-Difluoro-4-(2-phenylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acidYield 51%

Procedure

3-Chloromethyl-2-phenylsulfanyl-pyridine obtained in Step C of Preparation Example 15 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (21 mg, 0.09 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 (19 mg, 51%).

Workup

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

Sources & evidence

ORD record
ord-46d8dd121b6d408cab4191cbe4855496
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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