1-BROMOMETHYL-ISOQUINOLINE

Preparation 17-1); 1-Bromomethyl-isoquinolineTo 1-methylisoquinoline (0.99 g, 6.91 mmol), NBS (1.35 g, 1.1 eq) and AIBN(IO mg, catalytic amount) was added CCl (150 mg, 0.675 mmol) was dissolved in chloroform (15 mL) and cooled in water-ice bath m-chloroperoxobenzoic acid (77%, 0.230 g, 1.03 mmol) was added while stirring. The reaction mixture was let to gradually warm up to room temperature and stirred for 24 hours. The solvent was evaporated and the residue was purified by column chromatography on silica in methanol/ethyl acetate mixture. Fractions containing the product were evaporated to give 102 mg of product as pale yellow solid (0.430 mmol, 64 % yield relative to l-(bromomethyl)isoquinoline).'H NMR (CDC13, 25 C, 500 MHz): 5.17 (C//2-arom.. s, 2H); 7.61 ( arom ., ddd, 1H, 3/HH= 8 Hz, 3/HH= 7 Hz, 4/HH= 1 Hz); 7.64 (arom., d, 1H, 3/HH = 7 Hz); 7.73(arom., ddd, 1H, 3/HH = 9 Hz, 3/HH = 7 Hz, 4/HH = 1 Hz); 7.80-7.83 (arom., m, 1H);7.95 (arom., ddd, 1H, 3/HH= 9 Hz, 4/HH= 2 Hz, 4/HH= 1 Hz); 8.19 (arom., d, 1H, 3/HHNMR (CDC13, 25 C, 125 MHz): 5C20.9 (C//2-arom., s); 122.9 (arom., s); 124.0 (arom., s); 127.6 (arom., s); 127.8 (arom., s); 128.6 (arom., s); 128.8 (arom., s); 129.9 (arom., s); 136.9 (arom., s); 143.1 (arom., s).HRMS (ESI) m/z: [(M + H)+] (Ci0H9BrNO) calculated: 237.9862, found: 237.9863

Molecular Weight:222.08
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:220.98401
Monoisotopic Mass:220.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes