Potassium Fluoride → 6-Bromo-9H-pyrrolo[2,3-b:5,4-c′]dipyridine

A solution of 6′-bromo-2-fluoro-[3,4′]bipyridinyl-3′-ylamine (7.22 g, 26.9 mmol) in THF (75 mL) was added dropwise over 10 minutes to sodium bis-(trimethylsilyl)amide (1N solution in THF, 54 mL, 53.9 mmol). The reaction mixture was left to stir for 2.5 h then 1N aqueous potassium fluoride solution (7 mL) was added and the solvent evaporated in vacuo. The residue was diluted with water (100 mL) and the resultant solid was collected by filtration, washed with water (20 mL) and diethyl ether:pentane (1:1, 20 mL) and left to air dry. The resultant solid was triturated with methanol (50 mL), collected by filtration, washed with methanol (10 mL) and diethyl ether (20 mL) and pentane (20 mL) and left to air dry to afford the title compound as a brown solid (5.0 g, 75%). 1H NMR (DMSO-D6, 300 MHz): 8.73-8.69 (m, 2H), 8.63 (dd, J=4.8, 1.7 Hz, 1H), 8.48 (dd, J=1.0 Hz, 1H), 7.33 (dd, J=7.8, 4.8 Hz, 1H). LCMS (Method B): RT=2.43 min, M+H+=248/250.

1. waitThe reaction mixture was left
2. customthe solvent evaporated in vacuo
3. additionThe residue was diluted with water (100 mL)
4. filtrationthe resultant solid was collected by filtration
5. washwashed with water (20 mL) and diethyl ether:pentane (1:1, 20 mL)
6. waitleft to air
7. customdry
8. customThe resultant solid was triturated with methanol (50 mL)
9. filtrationcollected by filtration
10. washwashed with methanol (10 mL) and diethyl ether (20 mL) and pentane (20 mL)
11. waitleft to air
12. customdry

ORD record

ord-1ae3d4eb9fbf46e5b9c2108af4291a4b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2