Cesium carbonate → 6-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic Acid Methyl Ester

HRID 11710Notes

Reaction equation

HRID 11710 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([OH:28])[CH:3]=1.[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[N:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:28][C:4]2[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=2[O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[N:34][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 127522376-Bromomethyl-nicotinic acid methyl esterHCID 537887242-(4-Chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 696553196-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic Acid Methyl EsterYield 86.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.11 g, 0.27 mmol) in dioxane (1 mL) was added 6-bromomethyl-nicotinic acid methyl ester (0.075 g, 0.32 mmol) and cesium carbonate (0.15 g, 0.47 mmol). The reaction was stirred at ambient temperature for 6 days, then concentrated. Chromatography on silica gel gave the title compound (0.13 g).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-5d057237bfed40f38889c23a05bdd625
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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