2-Chloromethyl-6-cyclopentylsulfanyl-pyridine → {2-[4-(6-Cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropyl}-acetic acid

HRID 62991Notes

Reaction equation

HRID 62991 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](=[O:30])[CH2:18][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>>[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[CH2:18][C:17]([OH:30])=[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 901181812-Chloromethyl-6-cyclopentylsulfanyl-pyridineHCID 90118358[2-(3-Fluoro-4-hydroxy-phenyl)-cyclopropyl]-acetic acid methyl ester

Product 1

HCID 74221757{2-[4-(6-Cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropyl}-acetic acidYield 90.6%

Procedure

2-Chloromethyl-6-cyclopentylsulfanyl-pyridine (0.026 g, 0.11 mmol) obtained in Step C of Preparation Example 27 and [2-(3-fluoro-4-hydroxy-phenyl)-cyclopropyl]-acetic acid methyl ester (0.026 g, 0.11 mmol) obtained in Step F of Preparation Example 53 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.040 g, 87%).

Workup

  1. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-4a9192d1e2de4401a6c62e15c4e89c42
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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