5-Fluoro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine → [5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-fluoro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Participants

Reaction Conditions

Reaction Steps

5-Fluoro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (146, 0.33 g, 0.79 mmol) and 1.5 mL of tetrahydrofuran were combined in a round bottom flask and cooled to −20° C. Isopropylmagnesium chloride (400 μL, 2.0 M in tetrahydrofuran, 0.8 mmol) was added dropwise and the reaction stirred and brought to −5° C. The reaction was cooled to −20° C. and 5-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carbaldehyde (145, 0.090 g, 0.36 mmol) in tetrahydrofuran was added and the reaction stirred and brought to 0° C. The reaction was concentrated under vacuum, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, then brine. The organic layer was separated and dried over sodium sulfate, filtered and the filtrate purified by silica gel flash column chromatography eluting with a gradient of 5-80% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=542.7, 543.95.

Provenance & Evidence