Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoate → 3-[3-Chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid

HRID 62970Notes

Reaction equation

HRID 62970 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:16][C:17](=[O:29])[CH:18]([CH3:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([Cl:27])[CH:21]=1)C>>[Cl:27][C:22]1[CH:21]=[C:20]([CH2:19][CH:18]([CH3:28])[C:17]([OH:29])=[O:16])[CH:25]=[CH:24][C:23]=1[O:26][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

Participants

3

Reactant 2

HCID 58566718Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoateHCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridine

Product 1

HCID 742229723-[3-Chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acidYield 81%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (50 mg, 0.25 mmol) obtained in Step C of Preparation Example 23 and 3-(3-chloro-4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (60 mg, 0.28 mmol) obtained in Step B of Preparation Example 46 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (76 mg, 81%).

Workup

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

Sources & evidence

ORD record
ord-57c1d319f9bd4a699b300d9c0f7dbe13
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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