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

HRID 62940Notes

Reaction equation

HRID 62940 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:10][CH:11]2[CH2:15][CH2:14][CH2:13]C2)=[N:5][C:6](C)=[CH:7][CH:8]=1.C([O:18][C:19]([CH:21]1[CH2:23][CH:22]1[C:24]1[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([F:32])[CH:25]=1)=[O:20])C>>[CH:11]1([S:10][C:4]2[C:3]([CH2:2][O:31][C:27]3[C:26]([F:32])=[CH:25][C:24]([CH:22]4[CH2:23][CH:21]4[C:19]([OH:20])=[O:18])=[CH:29][C:28]=3[F:30])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 59419842Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylateHCID 901180413-Chloromethyl-2-cyclopentylsulfanyl-6-methyl-pyridine

Product 1

HCID 742225302-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acidYield 81.4%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.024 g, 0.113 mmol) obtained in Step C of Preparation Example 23 and 2-(3,5-difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.026 g, 0.113 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 (0.036 g, 81%).

Workup

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

Sources & evidence

ORD record
ord-78756920ade84c9f9652a87795358fcd
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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