2-Chloromethyl-6-cyclopentylsulfanyl-pyridine → 2-[3-Chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid

HRID 62975Notes

Reaction equation

HRID 62975 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[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([Cl:30])[CH:24]=1)=[O:19])C>>[Cl:30][C:25]1[CH:24]=[C:23]([CH:21]2[CH2:22][CH:20]2[C:18]([OH:19])=[O:17])[CH:28]=[CH:27][C:26]=1[O:29][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

Participants

3

Reactant 2

HCID 901181812-Chloromethyl-6-cyclopentylsulfanyl-pyridineHCID 901181992-(3-Chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester

Product 1

HCID 901180962-[3-Chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 72%

Procedure

2-Chloromethyl-6-cyclopentylsulfanyl-pyridine (42 mg, 0.18 mmol) obtained in Step C of Preparation Example 27 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (49 mg, 0.20 mmol) obtained in Step B of Preparation Example 47 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (47 mg, 72%).

Workup

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

Sources & evidence

ORD record
ord-2b8501c18ed04efa99bee137888086f5
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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