Sodium Bicarbonate → Ethyl 7-bromoisoquinoline-3-carboxylate

To a mixture of ethyl-3-(4-bromophenyl)-2-formamidopropanoate (23.5 g, 78 mmol) in DCM (200 mL) was added (CO)2Cl2 (8 ml, 84 mmol). The reaction mixture was stirred at r.t. for 30 mins. Then the reaction solution was cooled to 0° C. and FeCl3 (16 g, 98 mmol) was added into the solution, followed by stirring at r.t overnight. After the solution was extracted by CH2Cl2, the combined organic layers were concentrated in vacuo to afford a black oil. The oil was dissolved in the EtOH (100 ml), and concentrated H2SO4 was added into the solution and refluxed at 80° C. overnight. The solution was poured into saturated NaHCO3 and extracted by EA. After drying with anhydrous Na2SO4, the solution was concentrated in vacuo, and the residue was purified by silica gel chromatography (PE/EA=8:1 to 5:1) to afford ethyl 7-bromoisoquinoline-3-carboxylate as a yellow solid (5.2 g, yield: 23.8%).

1. temperatureThen the reaction solution was cooled to 0° C.
2. stirringby stirring at r.t overnight
3. extractionAfter the solution was extracted by CH2Cl2
4. concentrationthe combined organic layers were concentrated in vacuo
5. customto afford a black oil
6. additionwas added into the solution
7. temperaturerefluxed at 80° C. overnight
8. extractionextracted by EA
9. dry with materialAfter drying with anhydrous Na2SO4
10. concentrationthe solution was concentrated in vacuo
11. customthe residue was purified by silica gel chromatography (PE/EA=8:1 to 5:1)

ORD record

ord-c78fcc92a69e4b37b872a9b0081b71fa

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096549B2