Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-[4-(2-Cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid ethyl ester

HRID 62931Notes

Reaction equation

HRID 62931 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([OH:27])=[C:22]([F:28])[CH:21]=1)[CH3:15]>>[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([O:27][CH2:2][C:3]2[C:4]([S:9][CH2:10][CH:11]3[CH2:13][CH2:12]3)=[N:5][CH:6]=[CH:7][CH:8]=2)=[C:22]([F:28])[CH:21]=1)[CH3:15]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 901181843-Chloromethyl-2-cyclopropylmethylsulfanyl-pyridine

Product 1

HCID 901183033-[4-(2-Cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid ethyl esterYield 80%

Procedure

3-Chloromethyl-2-cyclopropylmethylsulfanyl-pyridine (0.07 g, 0.32 mmol) obtained in Step C of Preparation Example 18 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester obtained in Step D of Preparation Example 2 were reacted in the same manner as in Step A of Example 1 to obtain the title compound (0.1 g, 80%).

Workup

  1. customwere reacted in the same manner as in Step A of Example 1

Sources & evidence

ORD record
ord-425f3af3cfe34dfcbc3f90e140fad01b
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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