Sodium bis(trimethylsilyl)amide → 3-Bromo-6-chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole

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Reaction Steps

A solution of 5-bromo-6′-chloro-2-fluoro-[3,4]bipyridinyl-3′-ylamine (2.21 g, 7.32 mmol) in THF (124 mL) was added dropwise over 10 minutes to sodium bis-(trimethylsilyl)amide (1N solution in THF, 14.6 mL, 14.6 mmol). The reaction mixture was stirred for 1 h at ambient temperature and then quenched by the addition of water (2 mL). The resultant brown solution was partitioned between ethyl acetate (75 mL) and brine (50 mL). An off-white solid precipitated and was collected by filtration to afford the title compound as a grey solid (1.01 g, 49%). 1H NMR (DMSO-D5, 300 MHz): 9.01 (d, J=2.3 Hz, 1H), 8.73 (s, 1H), 8.70 (d, J=2.3 Hz, 1H), 8.35 (s, 1H). LCMS (Method B): RT=3.33 min, M+H+=284.

Provenance & Evidence