Ethyl 5-(chloromethyl)pyridine-2-carboxylate → 5-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester

HRID 1095929Notes

Reaction equation

HRID 1095929 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:23])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([OH:21])([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=1)[C:10]([F:13])([F:12])[F:11].[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([CH2:35]Cl)=[CH:31][N:30]=1)=[O:28])[CH3:25]>>[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:23][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([OH:21])([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:31][N:30]=1)=[O:28])[CH3:25]

Participants

3

Reactant 2

HCID 21698088Ethyl 5-(chloromethyl)pyridine-2-carboxylateHCID 252541463-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol

Product 1

HCID 469407315-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-pyridine-2-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to Example 93, step 7 from 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol (obtained in Example 93, step 6) by alkylation with ethyl-5-(chloromethyl)-pyridine-2-carboxylate [CAS Reg. No. 39977-48-5]. MS (m/e)=509.1 [MH+].

Sources & evidence

ORD record
ord-49c3b5bf13964c07b0dd5ade234de31c
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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