3-Chloromethyl-2-isopropylsulfanyl-pyridine → 2-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-benzyl]-cyclopropane carboxylic acid

HRID 62987Notes

Reaction equation

HRID 62987 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:15][C:16]([CH:18]1[CH2:20][CH:19]1[CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([OH:29])=[C:24]([F:30])[CH:23]=1)=[O:17])C>>[F:28][C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([F:30])[C:25]=1[O:29][CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH2:21][CH:19]1[CH2:20][CH:18]1[C:16]([OH:17])=[O:15]

Participants

3

Reactant 2

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineHCID 594555642-(3,5-Difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl ester

Product 1

HCID 742216692-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-benzyl]-cyclopropane carboxylic acidYield 79.1%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (0.019 g, 0.09 mmol) obtained in Step C of Preparation Example 1 and 2-(3,5-difluoro-4-hydroxy-benzyl]-cyclopropane carboxylic acid ethyl ester (0.023 g, 0.09 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 (0.028 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-6b69738fb3eb4cecbbfd71141a99cbd0
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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