Potassium Carbonate → 4-(2-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenoxy}-ethoxy)-benzoic acid methyl ester

HRID 1095869Notes

Reaction equation

HRID 1095869 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]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)[C:10]([F:13])([F:12])[F:11].Br[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:37][O:36][C:34](=[O:35])[C:31]1[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][O:23][C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([OH:21])([C:14]3[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=3)[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 1898264Methyl 4-(2-bromoethoxy)benzoateHCID 574212313-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol

Product 1

HCID 469406404-(2-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenoxy}-ethoxy)-benzoic acid methyl ester

Procedure

In analogy to Example 1, step 7, 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol (Example 1, step 6) was reacted with methyl 4-(2-bromoethoxy)benzenecarboxylate and potassium carbonate to give the title compound as a colorless viscous oil. MS (m/e)=524.9 [M+H+].

Sources & evidence

ORD record
ord-8c9453bc5a184608a0dccf0838d4d53f
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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