Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylate → 2-[4-(6-Cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid

HRID 62954Notes

Reaction equation

HRID 62954 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)[N:4]=1.C([O:16][C:17]([CH:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[C:26]([F:28])[C:25]([OH:29])=[C:24]([F:30])[CH:23]=1)=[O:18])C>>[CH:10]1([S:9][C:5]2[N:4]=[C:3]([CH2:2][O:29][C:25]3[C:24]([F:30])=[CH:23][C:22]([CH:20]4[CH2:21][CH:19]4[C:17]([OH:18])=[O:16])=[CH:27][C:26]=3[F:28])[CH:8]=[CH:7][CH:6]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 59419842Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylateHCID 901181462-Chloromethyl-6-cyclobutylsulfanyl-pyridine

Product 1

HCID 742227892-[4-(6-Cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acidYield 71%

Procedure

2-Chloromethyl-6-cyclobutylsulfanyl-pyridine (0.040 g, 0.18 mmol) obtained in Step C of Preparation Example 37 and 2-(3,5-difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.045 g, 0.18 mmol) obtained in Step B of Preparation Example 31 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.050 g, 69%).

Workup

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

Sources & evidence

ORD record
ord-88d126e83caa406ca1b5eadeea57400b
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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