Sodium Iodide → HCID 87258798, compound

HRID 1242302Notes

Reaction equation

HRID 1242302 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=1[C:15]([F:18])([F:17])[F:16])[CH3:2].Cl[CH2:21][C:22]1[C:23]([CH3:38])=[N:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1.[Na+].[I-].C1CCN2C(=NCCC2)CC1>CS(C)=O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:14])[CH2:21][C:22]2[C:23]([CH3:38])=[N:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)=[CH:9][C:8]=1[C:15]([F:17])([F:18])[F:16])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219357513-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine2×HCID 67072166HCID 67072166, compound

Product 1

HCID 87258798HCID 87258798, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 0.080 g (0.29 mmol) of the above prepared (4-methylamino-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester and 0.124 g (0.43 mmol) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (see example 1N], dissolved in 1.0 ml of abs. DMSO, were added successively 0.048 g (0.32 mmol) of NaI and 0.066 g (0.43 mmol) of DBU. The reaction was allowed to proceed for 4 h at ambient temperature, when TLC still indicated some starting amine. Therefore, another 33 mg (0.4 eq.) of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine was added and stirring continued for 3 h. Pouring onto crashed ice, extraction with AcOEt, filtration over Celite, washing of the organic layer with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2), afforded 0.046 g of the title compound as colorless oil.

Workup

  1. dissolutiondissolved in 1.0 ml of abs
  2. waitcontinued for 3 h
  3. additionPouring
  4. extractionice, extraction
  5. filtrationwith AcOEt, filtration over Celite
  6. washwashing of the organic layer with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7f32f42372a7414c9a72a07e89e0cc67
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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