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

HRID 62972Notes

Reaction equation

HRID 62972 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[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([Cl:28])[CH:22]=1)=[O:17])C>>[Cl:28][C:23]1[CH:22]=[C:21]([CH:19]2[CH2:20][CH:18]2[C:16]([OH:17])=[O:15])[CH:26]=[CH:25][C:24]=1[O:27][CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineHCID 901181992-(3-Chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester

Product 1

HCID 901181962-[3-Chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 80%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (33 mg, 0.16 mmol) obtained in Step C of Preparation Example 1 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (43 mg, 0.17 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 (42 mg, 80%).

Workup

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

Sources & evidence

ORD record
ord-6700a5250b074844827f60ef1b1f373f
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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