Lithium diisopropylamide → HCID 70977987, 화합물

참여 물질

반응 조건

반응 단계

A solution of 4-methyl-6-(thiazol-5-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)pyridin-2-amine (1.5 g, 4.46 mmol) in THF (35.7 mL) was cooled to −78° C. LDA (2M, 6.69 mL, 13.38 mmol) solution was slowly added, and the resulting mixture was stirred as at −78° C. for 30 minutes. In a separate dry flask, methyl 1-oxo-2,3-dihydro-1H-indene-5-carboxylate (1.06 g, 5.57 mmol) was dissolved in THF (5 mL), then this solution was added to the reaction mixture, which was then allowed to warm to rt over a period of 3 hrs, then stirred at rt for an additional 13 h. The reaction was quenched by addition of 2 mL MeOH and then loaded directly onto a silica gel chromatography column and purified with a gradient solvent system of 0-100% EtOAc/hexanes. The product-containing fractions were evaporated to give methyl 1-hydroxy-1-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-2,3-dihydro-1H-indene-5-carboxylate 16C (912 mg, 39%) as a light yellow solid. MS ESI calcd for C26H21F3N4O3S [M+H]+ 527, found 527.

출처 및 근거