Sodium Carbonate → ethyl 3-bromo-1-(1-ethoxyethyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate

1.19 g (3.81 mmol) of 3,5-dibromo-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxaldehyde are introduced with stirring into 50 mL of ethanol under an argon atmosphere at a temperature in the region of 20° C., followed by addition of 0.4 g (3.81 mmol) of sodium carbonate and 0.42 mL (3.81 mmol) of ethyl 2-mercaptoacetate. The reaction mixture is then refluxed for 2 hours, and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 60 mL of water and 60 mL of dichloromethane, and the phases are separated by settling. The organic phase is dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2.7 kPa). 1.17 g of ethyl 3-bromo-1-(1-ethoxyethyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate are thus obtained in the form of a pale yellow oil that crystallizes to give cream-colored crystals melting at 69° C.

1. temperatureThe reaction mixture is then refluxed for 2 hours
2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
3. custom60 mL of dichloromethane, and the phases are separated
4. dry with materialThe organic phase is dried over magnesium sulfate
5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

ORD record

ord-88ca9d07b3da498c976ceaf3c284ad3d

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07595320B2