3-Chloromethyl-2-isopropylsulfanyl-pyridine → 2-[3-Fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid

HRID 62961Notes

Reaction equation

HRID 62961 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[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])C>>[F:28][C:23]1[CH:22]=[C:21]([CH:19]2[CH2:20][CH:18]2[C:16]([OH:17])=[O:15])[CH:26]=[CH:25][C:24]=1[O:27][CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineHCID 585667072-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 742227952-[3-Fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acidYield 84%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (0.040 g, 0.20 mmol) obtained in Step C of Preparation Example 1 and 2-[3-fluoro-4-hydroxy-phenyl]-cyclopropane carboxylic acid ethyl ester (0.044 g, 0.20 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 (0.060 g, 84%).

Workup

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

Sources & evidence

ORD record
ord-6e8690af860246bba24af5ea12711eef
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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