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

HRID 62964Notes

Reaction equation

HRID 62964 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:17][C:18]([CH:20]1[CH2:22][CH:21]1[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:30])[CH:24]=1)=[O:19])C>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:29][C:26]3[CH:27]=[CH:28][C:23]([CH:21]4[CH2:22][CH:20]4[C:18]([OH:19])=[O:17])=[CH:24][C:25]=3[F:30])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 585667072-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl esterHCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 742228832-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acidYield 101.7%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.040 g, 0.17 mmol) obtained in Step C of Preparation Example 8 and 2-(3-fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.040 g, 0.17 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 (0.067 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-31271d8ebd184347942df46e1f194fa1
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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