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

HRID 62934Notes

Reaction equation

HRID 62934 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]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>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:29][C:25]3[C:24]([F:30])=[CH:23][C:22]([CH2:21][CH2:20][C:19]([OH:31])=[O:18])=[CH:27][C:26]=3[F:28])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 901181563-Chloromethyl-2-cyclohexylsulfanyl-pyridine

Product 1

HCID 742223683-[4-(2-Cyclohexylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acidYield 76.3%

Procedure

3-Chloromethyl-2-cyclohexylsulfanyl-pyridine (0.074 mmol) obtained in Step C of Preparation Example 22 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (17.5 mg, 0.074 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 (23 mg, 74%).

Workup

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

Sources & evidence

ORD record
ord-49e6dbb30008472b98e7b3c075a7041f
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…