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

HRID 62986Notes

Reaction equation

HRID 62986 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[CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([OH:30])=[C:25]([F:31])[CH:24]=1)=[O:18])C>>[CH:10]1([S:9][C:5]2[N:4]=[C:3]([CH2:2][O:30][C:26]3[C:25]([F:31])=[CH:24][C:23]([CH2:22][CH:20]4[CH2:21][CH:19]4[C:17]([OH:18])=[O:16])=[CH:28][C:27]=3[F:29])[CH:8]=[CH:7][CH:6]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 594555642-(3,5-Difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl esterHCID 901181462-Chloromethyl-6-cyclobutylsulfanyl-pyridine

Product 1

HCID 901181662-[4-(6-Cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-benzyl]-cyclopropane carboxylic acidYield 66%

Procedure

2-Chloromethyl-6-cyclobutylsulfanyl-pyridine (0.021 g, 0.10 mmol) obtained in Step C of Preparation Example 37 and 2-(3,5-difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl ester (0.024 g, 0.10 mmol) obtained in Step D of Preparation Example 49 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.026 g, 66%).

Workup

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

Sources & evidence

ORD record
ord-d2b8ae829c5b4ea6a9474c942520c7f0
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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