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

A solution of 5-bromo-2,6′-difluoro-[3,4′]bipyridinyl-3′-ylamine (0.79 g, 2.76 mmol) in THF (15 mL) was added dropwise over 10 minutes to sodium bis(trimethylsilyl)amide (1N solution in THF, 5.5 mL, 5.52 mmol). The reaction mixture was left to stir for 20 minutes then quenched by the addition of water (2 mL). The resultant black solution was partitioned between ethyl acetate (75 mL) and water (50 mL) and the layers separated. The organic phase was dried over sodium sulfate, filtered and evaporated in vacuo to give an off white solid. The resultant solid was triturated with ethyl acetate (30 mL), collected by filtration, washed with diethyl ether (5 mL) and left to air dry to afford the title compound as an off white solid (0.51 g, 65%). 1H NMR (DMSO-D6, 300 MHz): 9.00 (d, J=2.3 Hz, 1H), 8.69 (d, J=2.3 Hz, 1H), 8.51 (dd, J=1.7, 0.9 Hz, 1H), 7.95 (dd, J=2.4, 0.9 Hz, 1H). LCMS (Method B): RT=3.10 min, M+H+=266/268.

1. waitThe reaction mixture was left
2. customthen quenched by the addition of water (2 mL)
3. customThe resultant black solution was partitioned between ethyl acetate (75 mL) and water (50 mL)
4. customthe layers separated
5. dry with materialThe organic phase was dried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto give an off white solid
9. customThe resultant solid was triturated with ethyl acetate (30 mL)
10. filtrationcollected by filtration
11. washwashed with diethyl ether (5 mL)
12. waitleft to air
13. customdry

ORD record

ord-039fb25c5e0e40c1ba8c12571f9e6fb0

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216980B2