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

HRID 62979Notes

Reaction equation

HRID 62979 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]([CH3:28])[C:22]=1[CH3:29])=[O:17])C>>[CH:10]([S:9][C:4]1[C:3]([CH2:2][O:27][C:24]2[CH:25]=[CH:26][C:21]([CH:19]3[CH2:20][CH:18]3[C:16]([OH:17])=[O:15])=[C:22]([CH3:29])[C:23]=2[CH3:28])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineHCID 901180052-(4-Hydroxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 742229762-[4-(2-Isopropylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-cyclopropane carboxylic acidYield 81.3%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (0.030 g, 0.149 mmol) obtained in Step C of Preparation Example 1 and 2-(4-hydroxy-2,3-dimethyl-phenyl)-cyclopropane carboxylic acid ethyl ester (0.035 g, 0.149 mmol) obtained in Step C of Preparation Example 48 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.045 g, 81%).

Workup

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

Sources & evidence

ORD record
ord-20e48a7476e942228d061ac60c25767f
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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