Nitromethane → methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

Participants

Reaction Steps

To an oven-dried flask in ice bath was added AlCl3 (382 mg, 2.86 mmol), then CH2Cl2 (4 mL) was introduced at 0° C. Nitromethane (10.84 μL, 0.201 mmol) was added at that temperature. Ice bath was removed and the mixture was stirred at room temperature for 30 min. N-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)pivalamide (90 mg, 0.286 mmol) and methyl 2-chloro-2-oxoacetate (0.079 mL, 0.859 mmol) were added at 0° C. The reaction mixture was stirred for three hours at room temperature. The reaction mixture was quenched with ammonium acetate (8 mL) and extracted with ethyl acetate (3×10 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (40 mg, 45%) as white solid.

Provenance & Evidence