Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoate → 3-[3-Chloro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid

HRID 62968Notes

Reaction equation

HRID 62968 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=1.C([O:15][C:16](=[O:28])[CH:17]([CH3:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([Cl:26])[CH:20]=1)C>>[Cl:26][C:21]1[CH:20]=[C:19]([CH2:18][CH:17]([CH3:27])[C:16]([OH:28])=[O:15])[CH:24]=[CH:23][C:22]=1[O:25][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=1

Participants

3

Reactant 2

HCID 58566718Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoateHCID 901181412-Chloromethyl-6-isopropylsulfanyl-pyridine

Product 1

HCID 742229713-[3-Chloro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acidYield 89%

Procedure

2-Chloromethyl-6-isopropylsulfanyl-pyridine (35 mg, 0.17 mmol) obtained in Step C of Preparation Example 16 and 3-(3-chloro-4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (47 mg, 0.19 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 (50 mg, 89%).

Workup

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

Sources & evidence

ORD record
ord-2780b94fcd0a45d6b6fb59da3a225604
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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