3-Methoxyquinoline

General procedure: A 70 mL teflon-screw capped schlenk tube was charged with potassium carboxylate (1l-z) (1.00 mmol), copper(II) acetate (46 mg, 0.25 mmol), silver carbonate (276 mg, 1 mmol), and alkoxy borane (4a-h) (1.2 mmol). Anhydrous DMF (5 mL) was added, the reaction vessel was briefly purged with oxygen, and the resulting mixture was stirred at 140 °C for 36 h. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (20 mL) and washed with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with diethyl ether (3 x 20 mL), and the combined organic layers were washed with water, 5 N HCl and brine, dried over MgSOStep 1: To a solution of 3-bromoquinoline (3) (6.5 mL, 48 mmol)in dimethylformamide (80 mL) were added sodium methanolate30percent (16 mL, 54 mmol) and copper iodide (458 mg, 2.4 mmol). The mixture was refluxed for 16 h, hydrolyzed andextracted with Et2O. The organic layer was washed with waterand brine, dried over MgSO4 and evaporated under vacuum toafford 3-methoxyquinoline in 94percent yield as a colorless oil; 1HNMR (300 MHz, CDCl3) δ: 8.45 (d, 1H, 2.9 Hz), 7, 85 (d, 1H, 8.1 Hzand 1.2 Hz), 7.49 (d, 1H, 8.1 Hz and 1.2 Hz), 7.36-7.25 (m, 2H), 7.12 (d, 1H, 2.9 Hz), 3.67 (s, 3H); MS (APCI, pos. 30 V) m/z:[M+H]+, 160.A solution of Step 1: To a solution of 3-bromoquinoline (3) (6.5 mL, 48 mmol)in dimethylformamide (80 mL) were added sodium methanolate30percent (16 mL, 54 mmol) and copper iodide (458 mg, 2.4 mmol). The mixture was refluxed for 16 h, hydrolyzed andextracted with Et2O. The organic layer was washed with waterand brine, dried over MgSO4 and evaporated under vacuum toafford

Molecular Weight:159.18
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:159.068413911
Monoisotopic Mass:159.068413911
Topological Polar Surface Area:22.1
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes