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

HRID 62995Notes

Reaction equation

HRID 62995 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[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]([F:28])[CH:22]=1)=[O:17]>>[CH:11]1([CH2:10][S:9][C:4]2[C:3]([CH2:2][O:27][C:24]3[CH:25]=[CH:26][C:21]([CH:19]4[CH2:20][CH:18]4[C:16]([OH:17])=[O:15])=[CH:22][C:23]=3[F:28])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 901181192-(3-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterHCID 901181843-Chloromethyl-2-cyclopropylmethylsulfanyl-pyridine

Product 1

HCID 742228822-[4-(2-Cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acidYield 95%

Procedure

3-Chloromethyl-2-cyclopropylmethylsulfanyl-pyridine (0.026 g, 0.12 mmol) obtained in Step C of Preparation Example 18 and 2-(3-fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester (less polar) (0.025 g, 0.12 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 (0.042 g, 95%).

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-fb4d9e79ff9547f6943df7fdbaea7ecf
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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