2-(3,5-Difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester → 2-[4-(6-Cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid

HRID 63013Notes

Reaction equation

HRID 63013 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:15][C:16]([CH:18]1[CH2:20][CH:19]1[C:21]1[CH:26]=[C:25]([F:27])[C:24]([OH:28])=[C:23]([F:29])[CH:22]=1)=[O:17]>>[CH:10]1([S:9][C:5]2[N:4]=[C:3]([CH2:2][O:28][C:24]3[C:23]([F:29])=[CH:22][C:21]([CH:19]4[CH2:20][CH:18]4[C:16]([OH:17])=[O:15])=[CH:26][C:25]=3[F:27])[CH:8]=[CH:7][CH:6]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 901181212-(3,5-Difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterHCID 901181462-Chloromethyl-6-cyclobutylsulfanyl-pyridine

Product 1

HCID 742227892-[4-(6-Cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acidYield 88%

Procedure

2-Chloromethyl-6-cyclobutylsulfanyl-pyridine (0.018 g, 0.08 mmol) obtained in Step C of Preparation Example 37 and 2-(3,5-difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester (more polar) (0.020 g, 0.08 mmol) obtained in Step C of Preparation Example 60 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.030 g, 88%).

Workup

  1. customobtained in Step C of Preparation Example 60
  2. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-ec2f65c5b7f44291aa392cdd88c91acd
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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