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

HRID 1242295Notes

Reaction equation

HRID 1242295 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=1[CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH3:2].Cl[CH:22]([C:26]1[C:27]([CH3:42])=[N:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)=[CH:30][CH:31]=1)[CH2:23][CH2:24][CH3:25].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:14])[CH:22]([C:26]2[C:27]([CH3:42])=[N:28][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)=[CH:30][CH:31]=2)[CH2:23][CH2:24][CH3:25])=[CH:9][C:8]=1[CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21935942HCID 21935942, compoundHCID 670721342-(3-Methoxy-propyl)-4-methylamino-phenoxy-acetic acid ethyl ester

Product 1

HCID 670723052-(3-Methoxy-propyl)-4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butyl}-amino)-phenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 0.0944 g (0.336 mmol) of the above prepared (example 1H]) [2-(3-methoxy-propyl)-4-methylamino-phenoxy]-acetic acid ethyl ester and 0.100 g (0.305 mmol) of the above prepared [rac]-3-(1-chloro-butyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine, dissolved in 1.9 ml of abs. DMSO, were added successively 0.0505 g of K2CO3 (0.366 mmol) and 0.0503 g (0.336 mmol) of NaI. The reaction was allowed to proceed for 5 h at 50° 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=8/2), afforded 0.082 g of the title compound as light yellow oil.

Workup

  1. dissolutiondissolved in 1.9 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-15218726995541b398808ded8cab8f37
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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