Lithium diisopropylamide → HCID 70977464, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried flask was added 4-methyl-6-(thiazol-5-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)pyridin-2-amine (300 mg, 0.892 mmol) and THF (7.1 mL) and the solution was cooled to −78° C. LDA (1.34 mL, 2.68 mmol) was slowly added, and the resulting mixture was stirred for 30 minutes at −78° C. In a separate oven-dried flask, methyl 1-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (316 mg, 1.12 mmol) was then dissolved in THF (5 mL), and this solution was added to the reaction mixture, which was then allowed to warm to rt. over a period of 3 hours. The reaction was then quenched with MeOH (5 mL) and concentrated. Purification by chromatography on silica gel furnished methyl 1-bromo-5-hydroxy-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate 17A (210 mg, 38%) as a light yellow solid. MS ESI calcd for C27H22BrF3N4O3S [M+H]+ 619, found 619.

Provenance & Evidence