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

HRID 62982Notes

Reaction equation

HRID 62982 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:4]=1.C([O:17][C:18]([CH:20]1[CH2:22][CH:21]1[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([F:32])[CH:25]=1)=[O:19])C>>[CH:10]1([S:9][C:5]2[N:4]=[C:3]([CH2:2][O:31][C:27]3[C:26]([F:32])=[CH:25][C:24]([CH2:23][CH:21]4[CH2:22][CH:20]4[C:18]([OH:19])=[O:17])=[CH:29][C:28]=3[F:30])[CH:8]=[CH:7][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 594555642-(3,5-Difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl esterHCID 901181812-Chloromethyl-6-cyclopentylsulfanyl-pyridine

Product 1

HCID 742229772-[4-(6-Cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-benzyl]-cyclopropane carboxylic acidYield 88.2%

Procedure

2-Chloromethyl-6-cyclopentylsulfanyl-pyridine (0.023 g, 0.10 mmol) obtained in Step C of Preparation Example 27 and 2-(3,5-difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl ester (0.026 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 (0.037 g, 88%).

Workup

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

Sources & evidence

ORD record
ord-6249638fff9b467faa5681bb19b8653d
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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