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

HRID 62990Notes

Reaction equation

HRID 62990 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH2:10][CH2:11][CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=1.C[O:14][C:15]([CH:17]1[CH2:19][CH:18]1[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1)=[O:16]>>[F:27][C:22]1[CH:21]=[C:20]([CH:18]2[CH2:19][CH:17]2[C:15]([OH:16])=[O:14])[CH:25]=[CH:24][C:23]=1[O:26][CH2:2][C:3]1[C:4]([S:9][CH2:10][CH2:11][CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 901181192-(3-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterHCID 901182823-Chloromethyl-2-propylsulfanyl-pyridine

Product 1

HCID 901183422-[3-Fluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 48%

Procedure

3-Chloromethyl-2-propylsulfanyl-pyridine (0.016 g, 0.08 mmol) obtained in Step C of Preparation Example 14 and 2-(3-fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester (less polar) (0.017 g, 0.08 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 (0.014 g, 48%).

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-e38c0efc65fc4dc1b3568e4fbae16e5b
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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