7-BROMO-ISOQUINOLIN-1-YLAMINE

3-(5, 5-dimethyl-1, 3, 2-dioxaborinan-2-yl)-N, N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)benzenesulfonamide (80 mg, 0.12 mmol), Chloro[(Di(1-Adamantyl)-N-Butylphosphine)-2-(2-Aminobiphenyl)]Palladium(II) (7.7 mg, 0.011 mmol), Cesium Carbonate (112 mg, 0.344 mmol) and 7-Bromoisoquinolin-1-Amine (25.6 mg, 0.115 mmol) were weighed into a 1 dram vial and taken into the glove box. Toluene (1 mL) and Water (0.1 mL) were added and the mixture stirred at 110 C. for 18 hours. The organics were removed in the genevac under reduced pressure.7-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)isoquinolin-1-amine (Intermediate 111a) and isoquinolin-1-amine-7 boronic acid (Intermediate 111b) KOAc (264 mg, 2.69 mmol) was activated by adding it to a round bottom flask, which was then heated to 250C under vacuum for 2 min, and then allowed to cool to rt under vacuum for an additional 10 min, after which time a N2 atmosphere was continuously maintained. Dry DMSO (2 mL) was added, followed by the addition of commercially available 3-(5, 5-dimethyl-l, 3, 2-dioxaborinan-2-yl)-N, N-bis(4-methoxybenzyl)-2-(l-(4- methoxybenzyl)-lH-tetrazol-5-yl)benzenesulfonamide (80 mg, 0.12 mmol), Chloro[(Di(l- Adamantyl)-N-Butylphosphine)-2-(2-Aminobiphenyl)]Palladium(II) (7.7 mg, 0.011 mmol), Cesium Carbonate (1 12 mg, 0.344 mmol) and 7-Bromoisoquinolin- 1 -Amine (25.6 mg, 0.115 mmol) were weighed into a 1 dram vial and taken into the glove box. Toluene (1 mL) and Water (0.1 mL) were added and the mixture stirred at 110C for 18 hours. The organics were removed in the genevac under reduced pressure. To remove the PMB protecting group, TFA (1 mL) and Anisole (0.050 mL, 0.459 mmol) was added to the residue and the mixture stirred at 65C for 2.5 hours. The mixture was allowed to cool, and the volatile organics were removed in the genenvac undder reduced pressure. The crude product was purified using mass directed reverse phase HPLC. LC-MS [M+H]+: 368.

Molecular Weight:223.07
XLogP3:2.6
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