Methyl 3-(3'-fluoro-4'-hydroxyphenyl)propionate → 3-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acid

HRID 63006Notes

Reaction equation

HRID 63006 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:15][C:16](=[O:27])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:25][C:22]3[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][C:16]([OH:27])=[O:15])=[CH:20][C:21]=3[F:26])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 22558806Methyl 3-(3'-fluoro-4'-hydroxyphenyl)propionateHCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridine

Product 1

HCID 742217633-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acidYield 82%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 23 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.041 g, 82%).

Workup

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

Sources & evidence

ORD record
ord-4cbc68c16dd84a97a386d7f3062efb64
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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