2-(3-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester → 2-[4-(6-Cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid

HRID 62999Notes

Reaction equation

HRID 62999 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: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]>>[CH:10]1([S:9][C:5]2[N:4]=[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]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 901181192-(3-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterHCID 901181812-Chloromethyl-6-cyclopentylsulfanyl-pyridine

Product 1

HCID 901181142-[4-(6-Cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acidYield 77%

Procedure

2-Chloromethyl-6-cyclopentylsulfanyl-pyridine (0.033 g, 0.14 mmol) obtained in Step C of Preparation Example 27 and 2-(3-fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester (less polar) (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 64 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.043 g, 77%).

Workup

  1. customobtained in Step C of Preparation Example 64
  2. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-77d1edb652a14087b6e300bfc1251e6a
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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