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

HRID 1242283Notes

Reaction equation

HRID 1242283 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].[H-].[Na+].[Na+].[I-].Cl[CH2:26][C:27]1[C:28]([CH3:43])=[N:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1>CN(C=O)C>[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])[CH2:26][C:27]2[C:28]([CH3:43])=[N:29][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)=[CH:31][CH:32]=2)=[CH:9][C:8]=1[CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 219357513-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 670721342-(3-Methoxy-propyl)-4-methylamino-phenoxy-acetic acid ethyl ester

Product 1

HCID 67072320(2-(3-Methoxy-propyl)-4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.102 g (0.36 mmol) of the above prepared [2-(3-methoxy-propyl)-4-methylamino-phenoxy]-acetic acid ethyl ester, dissolved in 1.4 ml of abs. DMF, were added successively at 0° C. 0.017 g of NaH (60% in mineral oil, 1.2 eq.), 0.054 g (1 eq.) of NaI and 0.100 g (1 eq.) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (see below 1K]). The reaction was allowed to proceed for 5 Min. at 0° C. and for 0.5 h at ambient temperature. Pouring onto crashed ice/KHSO4, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=75/25), yielded 0.126 g of the title compound as light yellow oil.

Workup

  1. dissolutiondissolved in 1.4 ml of abs
  2. additionPouring
  3. extractionice/KHSO4, twofold extraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-c78d86e0138147f8b7cf935fccc96967
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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