Methyl iodide → HCID 69055843, compound

HRID 490740Notes

Reaction equation

HRID 490740 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:9][C:10]=1[CH2:11][CH3:12])[CH3:2].[CH:24]([N-]C(C)C)(C)C.[Li+].CI>O1CCCC1>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=2)[S:9][C:10]=1[CH2:11][CH3:12])[CH3:24])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 69056840HCID 69056840, compound

Product 1

HCID 69055843HCID 69055843, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (2.02 g, 6.13 mmol) is dissolved into anhydrous tetrahydrofuran (THF) (10 mL) and lithium diisopropylamide (LDA) is slowly added at room temperature. This solution is allowed to stir at room temperature and monitored by TLC. After complete conversion, methyl iodide (582 mg, 4.00 mmol) is added slowly and the reaction is followed by TLC. After 18 h., the reaction is not complete, but is quenched with saturated ammonium chloride solution and diluted with diethyl ether. The two phases are separated and the organic layer is washed with water and brine, dried over anhydrous sodium sulfate, then concentrated and purified using flash column chromatography (10% EtOAc/Hexanes). The pure 2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid ethyl ester (1.30 g, 3.64 mmol) is obtained in 59% yield.

Workup

  1. additionis slowly added at room temperature
  2. customis quenched with saturated ammonium chloride solution
  3. additiondiluted with diethyl ether
  4. customThe two phases are separated
  5. washthe organic layer is washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-02eb28ba5c504604a53f3968bd7b1a73
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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