Diethyl Ether → 2,6-Difluoro-N-(4-(2-hydroxypropan-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

Reaktionsgleichung

[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10](C(OC)=O)[N:11]=1)=[O:5].[CH3:31][Mg+].[Br-].CC[O:36][CH2:37][CH3:38]>>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10]([C:37]([OH:36])([CH3:38])[CH3:31])[N:11]=1)=[O:5]

Komponenten

Edukt 3

HCID 3283Diethyl Ether

HCID 24765114Methyl 2-(2,6-difluorobenzamido)-5-(3-(trifluoromethyl)phenyl)thiazole-4-carboxylate

HCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 247655782,6-Difluoro-N-(4-(2-hydroxypropan-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideAusbeute 91 %

Versuchsvorschrift

Into a solution of Compound 35 (100 mg, 0.24 mmol) in 5 mL of Et2O was added dropwise MeMgBr (1.0 M solution in THF, 1.2 mL) at 0° C. The mixture was stirred at room temperature for 1 hour and quenched with 10 mL of H2O. The solution was extracted with Et2O. The combined extracts were dried and concentrated. The residue was purified by column chromatography on silica gel (10-70% EtOAc in hexanes) to give Compound 68 (91 mg, 91%) as a white solid.