2-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl ester → 2-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid

HRID 62965Notes

Reaction equation

HRID 62965 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:16][C:17]([CH:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([F:29])[CH:23]=1)=[O:18])C>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:28][C:25]3[CH:26]=[CH:27][C:22]([CH:20]4[CH2:21][CH:19]4[C:17]([OH:18])=[O:16])=[CH:23][C:24]=3[F:29])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 585667072-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl esterHCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridine

Product 1

HCID 742228842-[4-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acidYield 102.6%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (0.040 g, 0.18 mmol) obtained in Step C of Preparation Example 23 and 2-(3-fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.046 g, 0.18 mmol) obtained in Step C of Preparation Example 44 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.069 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-9e5b11e716fc4473ac1fcffbd2150981
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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