Acetonitrile → HCID 86646688, compound

Temperature

110 °C

Step 3—A mixture of 2 (0.9 g, 3.912 mmol), K2CO3 (0.595 g, 4.303 mmol) and 1,4-dibromobutane (0.49 mL, 4.108 mmol) in 14 mL of CH3CN and 1 mL of H2O was stirred at 110° C. for 30 minutes under microwave irradiation before being cooled to RT. 0.5 more equivalents of 1,4-dibromobutane were added and the resulting mixture was stirred at 110° C. for 30 minutes under microwave irradiation a second time before being cooled to RT. The reaction mixture was extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-8% EtOAc) to give 0.25 g of 3: 3-bromo-5-pyrrolidin-1-yl-benzoic acid methyl ester (22% yield).

1. temperaturebefore being cooled to RT
2. stirringthe resulting mixture was stirred at 110° C. for 30 minutes under microwave irradiation a second time
3. temperaturebefore being cooled to RT
4. extractionThe reaction mixture was extracted twice with DCM
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by SiO2 chromatography (hexanes/EtOAc 0-8% EtOAc)

ORD record

ord-a7fe6812273c45c6aed870a8ad795090

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008298B2