Bromine → 3-Bromo-4-chlorofuro[3,2-c]pyridine

To the solution of 4-chloro-furo[3,2-c]pyridine (4.2 g, 0.03 mol) In CCl4 (77 ml) was added Br2 (2.4 ml, 0.046 mol) at 0° C. and the resultant reaction mixture was stirred for 4 hours at room temperature. The resultant suspension was poured into the mixture of ethyl acetate and 10% Na2SO3. The corresponding organic phase was separated and dried over Na2SO4 and concentrated in vacuo. The crude residue was dissolved in THF (100 ml) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (5.6 ml) was added at 0° C. The resultant reaction mixture was stirred for 2 hours at room temperature and poured into NaHCO3 and ethyl acetate. The organic layers were separated, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on a silica gel column to afford the titled compound (5.4 g) 1H NMR (400 MHz, CDCl3) ppm 8.32 (d, J=5.8 Hz, 1H), 7.72 (s, 1H), 7.44 (d, J=5.8 Hz, 1H), 7.26 (s, 1H).

1. customthe resultant reaction mixture
2. customThe corresponding organic phase was separated
3. dry with materialdried over Na2SO4
4. concentrationconcentrated in vacuo
5. dissolutionThe crude residue was dissolved in THF (100 ml)
6. additionDBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (5.6 ml) was added at 0° C
7. customThe resultant reaction mixture
8. stirringwas stirred for 2 hours at room temperature
9. customThe organic layers were separated
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated to dryness
13. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-08c02a008e024afaae70f687922f4a1c

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592352B2