3-BROMO-6-METHOXYQUINOLINE

General procedure: To a solution of 6-substituted or 7-substituted 3-bromoquinoline (17-23, 1.0 mmol), N-(but-3-enyl)phthalimide (0.22 g, 1.1 mmol), NaOAc (0.14 g, 2.0 mmol) and PPh3 (31 mg, 0.12 mmol) in 4 mL of DMF was added Pd(OAc)2 (9 mg, 0.04 mmol) at room temperature under Ar condition. The mixture was heated to 120 C and stirred at 120 C overnight. The reaction solution was allowed to cool to room temperature and diluted with 100 mL of DCM, washed with brine (6×100 mL), dried with Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE: EA = 4: 1) to give 24-30, as a white solid.[00187] To G (92.5 mg, 0.244 mmol) in MeCN (2 mL) was added AgF (61.8 mg, 0.488 mmol, 2 equiv) and N-bromosuccinimide (47.8 mg, 0.268 mmol, 1.1 equiv), and the mixture was stirred at room temperature for 3 h. The mixture was then filtered, diluted with ethyl acetate (3 mL), and washed with saturated NaHCC (4 mL). The aqueous layer was extracted with ethyl acetate (4 mL), the combined organic layer washed with brine, dried with MgS04, filtered, and the solvents were evaporated. The residue was purified by preparative TLC (2:8 ethyl acetate:hexanes) to afford the product as a colorless solid (37.4 mg, 64% yield). H NMR (500 MHz, CDCI3) delta 8.72 (d, J= 2.1 Hz, IH), 8.16 (d, J = 1.8 Hz, IH), 7.94 (d, J Hz, 1H), 7.34 (dd, J = 9.2, 2.7 Hz, IH), 6.93 (d, J= 2.6 Hz, 1H), 3.90 (s, 3H). i 3C N.V1 R (126 MHz, CDClj) delta 158.59 (s), 148.81 (s), 142.57 (s), 136.02 (s), 130.96 (s), 130.43 (s), 122.76 (s), 1 17.83 (s), 104.30 (s), 55.71 (s). HRMS (ESI+) calcd for [Ci0H9BrNO ] (M+H ): 237.9862, fbimdi 237.9861.General procedure: To a solution of 6-substituted or 7-substituted quinoline (14 mmol) in 20 mL of CCl4 was added Br2 (14 mmol) dropwise at room temperature. The mixture was heated to reflux and pyridine was added (14 mmol). The reaction solution was refluxed for another 2 h. The mixture was allowed to cool to room temperature, diluted with 50 mL of DCM, washed with 50 mL of water and brine, dried with Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE: EA = 40: 1) to give 17-23, as an offwhite solid.

Molecular Weight:238.08
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:236.97893
Monoisotopic Mass:236.97893
Topological Polar Surface Area:22.1
Heavy Atom Count:13
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes