1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-Butyl (1R,2S)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

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Reaction Steps

A solution of cis-tert-butyl 2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (135.8 mg, 0.247 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (154 mg, 0.742 mmol) and bis(triphenylphosphine)palladium chloride (174 mg, 0.247 mmol) in dioxane (2 mL) and saturated aq Na2CO3 (2 mL) was heated at 120° C. for 30 min. After filtering out the solids, the solvent was removed and the residue was dissolved in MeOH and DCM and the mixture was purified by preparative HPLC. The fractions were collected and the solvent was stripped to dryness via rotary evaporation to give the title compound (109 mg, 74%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.97-1.98 (m, 10H), 2.28-2.44 (m, 3H), 2.56-2.72 (m, 4H), 3.63-3.99 (m, 11H), 4.36 (d, J=18.06 Hz, 2H), 4.56 (br s, 2H), 6.50 (br s, 1H), 6.61 (br s, 1H), 6.65-6.81 (m, 1H), 7.08 (br s, 1H), 7.70 (br s, 1H), 8.30 (br s, 1H), 8.75-9.02 (m, 1H). [M+H] calc'd for C31H39FN6O5, 595. found, 595.

Provenance & Evidence