Nitrogen → 6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridine

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Reaction Steps

To an N2 charged microwave vial, 6-bromo-1H-pyrrolo[3,2-b]pyridine (327 mg, 1.65 mmol) was added and dissolved in DMA (2 mL). The solution was bubbled with N2 for 5 minutes. Next, 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (516 mg, 2.48 mmol) was added to the solution, which was bubbled with N2 for an additional 5 minutes. K2CO3 (320 mg, 2.31 mmol) was dissolved in water (2 ml) and the solution was bubbled with N2 for 5 minutes. The aqueous solution was added to the reaction vessel and the solution was bubbled with N2 again. Finally, the Pd(dppf)2Cl2 (81 mg, 0.10 mmol) was added to the solution, bubbled with N2, sealed and microwaved for 15 minutes at 130° C. The reaction was then transferred to a separatory funnel with dichloromethane (75 mL) and washed with water (2×75 mL). The aqueous layer was back extracted with dichloromethane (75 mL). The organic layers were combined, dried over Na2SO4 and vacuumed down. The crude material was purified by flash chromatography (0-80% acetonitrile/dichloromethane gradient) to afford the title compound (200 mg, 61% yield). MS m/z=199 [M+H+]+.

Provenance & Evidence