HCID 86598134, compound → HCID 69054489, compound

HRID 860621Notes

Reaction equation

HRID 860621 reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:21]([CH3:23])[CH3:22])=[O:5].[CH3:25][Mg]Br>O1CCCC1>[CH:21]([C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:15][CH:16]=2)[S:10][C:6]=1[C:4](=[O:5])[CH3:25])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 86598134HCID 86598134, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69054489HCID 69054489, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid methoxy-methyl-amide (7.56 g, 21.09 mmol) is suspended in anhydrous tetrahydrofuran (100 mL), and cooled to 0° C. with stirring under nitrogen. Methyl magnesium bromide (28 mL, 3.0M in diethyl ether, 84.36 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully neutralized with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 1-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanone (5.4 g, 17.23 mmol) 82% yield, is used without further purification.

Workup

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3c034144467443499b31508bde644c78
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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