Sodium Iodide → HCID 69217922, compound

HRID 1393114Notes

Reaction equation

HRID 1393114 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:9][O:10][C:11](=[O:23])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[CH:16][C:15]=1[I:22].Cl[CH2:25][C:26]1[S:30][C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)=[N:28][C:27]=1[CH3:41]>CS(C)=O.CCOCC>[CH3:9][O:10][C:11](=[O:23])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:21])[CH2:25][C:26]2[S:30][C:29]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=3)=[N:28][C:27]=2[CH3:41])=[CH:16][C:15]=1[I:22]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 69220182HCID 69220182, compound

Product 1

HCID 69217922HCID 69217922, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of potassium carbonate (45 mg, 0.33 mmol), sodium iodide (45 mg, 0.30 mmol) and of (2-iodo-4-methylamino-phenoxy)-acetic acid methyl ester (73 mg, 0.35 mmol) in DMSO (4 ml) was treated with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (96 mg, 0.30 mmol, WO02/28433) in 3 portions over 1.5 h. The reaction mixture was stirred for total 2.5 h at RT, taken up in ether and washed with KHSO4-solution (10%). The organic phase was washed with NaCl (10%), dried (Na2SO4) and evaporated. Purification by flash chromatography (SiO2, n-heptane/AcOEt=4/1) gave 151 mg of pure (2-iodo-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester, MS: 577.2 (MH)+.

Workup

  1. washwashed with KHSO4-solution (10%)
  2. washThe organic phase was washed with NaCl (10%)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification by flash chromatography (SiO2, n-heptane/AcOEt=4/1)

Sources & evidence

ORD record
ord-a8a0a45dd1764a5390377a638636cf48
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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