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

HRID 62997Notes

Reaction equation

HRID 62997 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=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[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=1

Participants

3

Reactant 2

HCID 901181192-(3-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterHCID 901181412-Chloromethyl-6-isopropylsulfanyl-pyridine

Product 1

HCID 901181022-[3-Fluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 93%

Procedure

2-Chloromethyl-6-isopropylsulfanyl-pyridine (0.029 g, 0.14 mmol) obtained in Step C of Preparation Example 16 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 (0.048 g, 93%).

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-e087bc6819bf4277baf258c1f6ec4c7f
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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