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

A solution of 4-chlorofuro[3,2-c]pyridine (10.60 g, 69 mmol, 1.0 eq) in carbon tetrachloride (135 mL) was cooled to −15° C. and bromine (12.13 g, 80 mmol, 1.2 eq) was added drop-wise over a fifteen minute time period. The mixture was stirred at ambient temperature for eighteen hours. The solvent was removed in vacuo, and the residue was dissolved in methanol (250 mL). A solution of 20% aqueous sodium hydroxide (35 mL) was added and the mixture was stirred 1 hour at ambient temperature. The methanol was removed in vacuo, and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The layers were separated and the aqueous phase was extracted with dichloromethane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give the title compound (15.45 g, 96%) as a solid. 1H NMR (DMSO-d6,400 MHz) δ 8.54 (s, 1H), 8.37 (d, 1H), 7.87 (d, 1H); RP-HPLC (Conditions f) Rt 11.46 min.; MS: MH+ 232, 234.

1. customThe solvent was removed in vacuo
2. dissolutionthe residue was dissolved in methanol (250 mL)
3. additionA solution of 20% aqueous sodium hydroxide (35 mL) was added
4. stirringthe mixture was stirred 1 hour at ambient temperature
5. customThe methanol was removed in vacuo
6. customthe residue was partitioned between water (100 mL) and dichloromethane (50 mL)
7. customThe layers were separated
8. extractionthe aqueous phase was extracted with dichloromethane (50 mL)
9. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
10. customthe solvent was removed in vacuo

ORD record

ord-5a4567eec46e40288550aa2ae69b58ed

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737160B2