2-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol → 3-(4-{2-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yl)-propionic acid ethyl ester

HRID 1726993Notes

Reaction equation

HRID 1726993 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2].[CH3:19][C:20]1[C:25]([CH2:26][CH2:27]O)=[CH:24][CH:23]=[C:22]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[N:21]=1>>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:27][CH2:26][C:25]2[C:20]([CH3:19])=[N:21][C:22]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][CH:30]=3)=[CH:23][CH:24]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 219358312-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanolHCID 58566550Ethyl 3-(4-hydroxynaphthalen-1-yl)propanoate

Product 1

HCID 690415633-(4-{2-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yl)-propionic acid ethyl ester

Procedure

In analogy to the procedures described in example 4D] and 4E], 3-(4-hydroxy-naphthalen-1-yl)-propionic acid ethyl ester [Helvetica Chimica Acta (2001), 84(8), 2198-2211] was reacted with 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol (example 4K]) to give 3-(4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yl)-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless solid.

Sources & evidence

ORD record
ord-e12fdb28a89c43ed9d828378da084d39
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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