3-Chloromethyl-2-isopropylsulfanyl-pyridine → 3-[3-Chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid

HRID 62955Notes

Reaction equation

HRID 62955 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[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]([Cl:26])[CH:20]=1)C>>[Cl:26][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][C:16]([OH:27])=[O:15])[CH:24]=[CH:23][C:22]=1[O:25][CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineHCID 68766162Ethyl 3-(3-chloro-4-hydroxyphenyl)propanoate

Product 1

HCID 901180203-[3-Chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acidYield 101.9%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (23 mg, 0.11 mmol) obtained in Step C of Preparation Example 1 and 3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (29 mg, 0.12 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 (41 mg, 93%).

Workup

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

Sources & evidence

ORD record
ord-f68cf79ade48461d92f3c5d029fa5684
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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