Sodium Iodide → [Rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

HRID 1726971Notes

Reaction equation

HRID 1726971 reaction equation
Cl[CH:2]([C:5]1[C:6]([CH3:21])=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:9][CH:10]=1)[CH2:3][CH3:4].[CH2:22]([O:24][C:25](=[O:40])[CH2:26][O:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([NH:38][CH3:39])=[CH:30][CH:29]=1)[CH3:23].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CS(C)=O>[CH2:22]([O:24][C:25](=[O:40])[CH2:26][O:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([N:38]([CH3:39])[CH:2]([C:5]2[C:6]([CH3:21])=[N:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[CH:9][CH:10]=2)[CH2:3][CH3:4])=[CH:30][CH:29]=1)[CH3:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21935878[Rac]-3-(1-chloro-propyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridineHCID 69037388(4-Methylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

Product 1

HCID 69036795[Rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 0.164 g (0.523 mmol) of [rac]-3-(1-chloro-propyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine (see below 2C]) and 0.149 g (0.575 mmol) of the above prepared (4-methylamino-naphthalen-1-yloxy)-acetic acid ethyl ester, dissolved in 3.2 ml of abs. DMSO, were added successively 0.0867 g of K2CO3 (0.627 mmol) and 0.0856 g (0.575 mmol) of NaI. The reaction was allowed to proceed for 15 h at 60° C. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), yielded 0.043 g of the title compound as light yellow oil.

Workup

  1. dissolutiondissolved in 3.2 ml of abs
  2. additionPouring
  3. extractionice/NH4Cl, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-b79ed56ecd734a1691748543379345b8
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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