1,4-DIBROMOISOQUINOLINE

A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 °C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. RPreparation of Intermediate A: A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 In a 250ml three neck flask fitted with overhead stirrer and condenser which is also connected to a scrubber solution, 1-hydroxyisoquinoline (lO.g, 68.89mmol) and PBrs (53.38g, 124 mmol) were taken. The reaction mixture was gradually heated to 140°C. At about 125°C - 130°C the solid melts and a deep read solution obtained which on further heating converts to yellowish solid at ~135°C. The reaction mixture was heated at this temperature for lOmin then allowed to cool to room temperature. The pale yellow solid was crushed and added in portions into ice with stirring to obtain a pale yellow powder which was filtered and washed with water (150ml) and dried in an oven at 50°C under vacuum. The crude solid was purified by recrystallisation from EtOAc/heptane (14. lg, 99.93percent HPLC, 71.3percent yield). 1H-NMR (600MHz, CDCIGeneral procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBrA mixture of 2.90 g, 19.07 mMol of isocarbostyril and 14.40 g, 33.68 mMol of phosphorus pentabromide were allowed to melt together at 140° C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. R

Molecular Weight:286.95
XLogP3:3.8
Hydrogen Bond Acceptor Count:1
Exact Mass:286.87682
Monoisotopic Mass:284.87887
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes