[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine → [Rac]-(4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yloxy)-acetic acid ethyl ester

HRID 1727003Notes

Reaction equation

HRID 1727003 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O: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].Cl[CH:20]([C:22]1[C:23]([CH3:38])=[N:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1)[CH3:21]>>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH:20]([C:22]2[C:23]([CH3:38])=[N:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)[CH3:21])=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 69037588(4-Hydroxy-naphthalen-1-yloxy)-acetic acid ethyl ester

Product 1

HCID 69037414[Rac]-(4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yloxy)-acetic acid ethyl ester

Procedure

In analogy to the procedures described in example 5C] and 5D], (4-hydroxy-naphthalen-1-yloxy)-acetic acid ethyl ester was reacted with [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example 1L]) to give [rac]-(4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-1-yloxy)-acetic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow solid.

Sources & evidence

ORD record
ord-3f3266f823594f8d9e427cb5cda095c2
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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