4-BROMO-1-IODOISOQUINOLINE synthesis

Yield:-

Reaction Conditions:

with acetyl chloride;sodium iodideReflux;

Steps:

2

A flask containing 1,4-dibromoisoquinoline (5.0 g, 17.4 mmol), Nal (10.4 g, 69.7 mmol) and acetyl chloride (2.05 g, 26.1 mmol) was heated to reflux overnight. Upon cooling the reaction was quenched with H₂O and then carefully basified with sat. NaHCO₃. The organics were extracted with EtOAc (2×), washed with sat. NaCI and dried over MgSO₄. The solvent was removed in vacuo and the residual oil purified on the Biotage (5-10% EtOAc/hexanes) yielding 3.04 g (9.10 mmol) of 4-bromo-1-iodoisoquinoline. ¹H NMR (400 MHz, CDCl₃) δ 8.45 (s, 1H), 8.12-8.08 (m, 2H), 7.83 (m, 1H), 7.73 (m, 1H) ppm.

References:

US2010/222345,2010,A1 Location in patent:Page/Page column 97