2-Bromoethanol → HCID 57588283, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-(2H-tetrazol-5-yl)pyridine (WO 0194342 A1) (1.2 g, 5.3 mmol) was dissolved/suspended in 1-propanol (15 ml), a solution of potassium hydroxide (250 mg, 4.5 mmol) in 1-propanol (15 ml) was added and it was heated at 80° C. for 1 hour. 2-Bromoethanol (0.344 ml, 4.8 mmol) was added and it was refluxed for one day. Further potassium hydroxide (270 mg) and 2-bromoethanol (0.35 ml) were added and the mixture was heated for another 4 hours at reflux. Further potassium hydroxide and 2-bromoethanol were added once more and the mixture was refluxed for 14 hours. The reaction mixture was filtered through a 0.45 μM membrane and the filter cake was washed with ethanol and dichloromethane. Chromatography on silica gel with hexanes/ethyl acetate 1:1 to ethyl actetate gave 0.342 g of the title compound (24%), together with 0.225 g of the corresponding 1H-tetrazole regioisomer.

Provenance & Evidence