5-BROMO-8-ISOQUINOLINEAMINE

To a solution of A 3-neck flask was charged with 5-bromo-8-nitroisoquinoline (4g, 15.8mmol) and dissolved in MeOH (5OmL). A condenser was affixed and the mixture was heated to 100 0C. Aqueous (2OmL) solution of ammonium chloride (4.12g, 79mmol) was added slowly, followed by iron powder (3g, 53.7mmol). The heterogeneous mixture was stirred at 100 0C for 3h. LCMS confirmed complete reduction to the amine. The mixture was filtered and the solution was concentrated under reduced pressure to give a brown solid as crude product (2.4g, 68%). LCMS showed an m/z of 225.0/223.0 with a retention time of 0.767min, method [I]. 1.99.3. 5-Bromo-8-fluoroisoquinolineGeneral procedure: S7 (0.35 g, 2 mmol) was dissolved in Et2O (5 mL) and converted into its hydrochloride salt by drop-wise addition of aq. HCl (1 M) in Et2O. The resulting precipitate was collected byfiltration, dried for 10 min, and used in the subsequent reaction. A mixture of S7 hydrochloride (212 mg, 1 mmol), S1 (185 mg, 1.1 mmol), and toluene (2 mL) was heated to 130 oC, stirred for 21 h, cooled to rt, and diluted with MeOH (5 mL). This solution was concentrated onto silicagel and purified on a silica gel column with gradient elution (EtOAc EtOAc-MeOH;4: 1 v/v). The fractions containing the desired guanidine were collected, concentrated under reduced pressure, andapplied to a second silica gel column eluted with Et3N-EtOAc-hexanes(5: 20: 75 by vol.) to afford 20 asa white solid

Molecular Weight:223.07
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:221.97926
Monoisotopic Mass:221.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes