Ethyl 3-(3-fluoro-4-hydroxyphenyl)propionate → 3-[4-(6-Cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-propionic acid

HRID 63012Notes

Reaction equation

HRID 63012 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)[N:4]=1.C([O:16][C:17](=[O:28])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1)C>>[CH:11]1([CH2:10][S:9][C:5]2[N:4]=[C:3]([CH2:2][O:26][C:23]3[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][C:17]([OH:28])=[O:16])=[CH:21][C:22]=3[F:27])[CH:8]=[CH:7][CH:6]=2)[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 3023769Ethyl 3-(3-fluoro-4-hydroxyphenyl)propionateHCID 901183042-Chloromethyl-6-cyclopropylmethylsulfanyl-pyridine

Product 1

HCID 901181233-[4-(6-Cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-propionic acidYield 86%

Procedure

2-Chloromethyl-6-cyclopropylmethylsulfanyl-pyridine (0.030 g, 0.14 mmol) obtained in Step D of Preparation Example 20 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.043 g, 86%).

Workup

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

Sources & evidence

ORD record
ord-beb32e5510e34e648ea8ec055981d393
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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