5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine → (5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask, 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (4, 1.7 g, 3.9 mmol) was combined with 1.3 mL of tetrahydrofuran and cooled to −20° C. Isopropylmagnesium chloride (2.0 mL, 2 M in tetrahydrofuran, 4.0 mmol) was added dropwise and the reaction stirred at −5° C. The reaction was cooled to −20° C. and 5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehyde (113, 0.622 g, 1.83 mmol) in 2 mL of tetrahydrofuran was added and the reaction stirred at 0° C. The reaction was concentrated under vacuum, diluted with ethyl acetate and washed with sodium bicarbonate and brine. The organic layer was dried with sodium sulfate and purified by silica gel column chromatography, eluting with 5-80% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=648.38 and 649.74.

Provenance & Evidence