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

HRID 63018Notes

Reaction equation

HRID 63018 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:10][CH:11]([CH3:13])[CH3:12])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C([O:16][C:17](=[O:28])[CH2:18][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][CH2:18][C:17]([OH:28])=[O:16])[CH:25]=[CH:24][C:23]=1[O:26][CH2:2][C:3]1[C:4]([S:10][CH:11]([CH3:13])[CH3:12])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 68766162Ethyl 3-(3-chloro-4-hydroxyphenyl)propanoateHCID 901181983-Chloromethyl-2-isopropylsulfanyl-6-methyl-pyridine

Product 1

HCID 742218523-[3-Chloro-4-(2-isopropylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acidYield 58%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-6-methyl-pyridine (34 mg, 0.17 mmol) obtained in Step D of Preparation Example 9 and 3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (43 mg, 0.18 mmol) obtained in Step C of Preparation Example 42 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (32 mg, 58%).

Workup

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

Sources & evidence

ORD record
ord-5a7ca71b1b1245aa9307fb3ebd114c26
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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