Reference of 20555-91-3,Some common heterocyclic compound, 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, molecular formula is C6H3Cl2I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: In a 10 mL glass screw cap tube capped with a rubber septum, palladium acetate Pd(OAc)2, (5 mg, 0.023 mmol), 1,3-bis(diphenylphosphino)propane dppp, (9 mg, 0.023 mmol) were introduced under argon atmosphere. Then, 3 mL of freshly distilled toluene) were added under argon. The mixture was stirred for 10 min to allow formation of the catalyst. Then securinine 1 (100 mg, 0.46 mmol), potassium carbonate (K2CO3, 127 mg, 0.92 mmol) and the desired iodoarene (0.92 mmol) were added. The septum was replaced by a screw cap, and the mixture was stirred at 130 C, in an oil bath. After 24 h stirring, the reaction mixture was brought to room temperature and diluted with ethyl acetate (5 mL). The reaction mixture was filtered through a pad of Celite eluting with AcOEt (20 mL). The organic layer was extracted with a saturated aqueous solution of sodium hydrogen carbonate (10 mL) and brine (10 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification by flash column chromatography on silica gel (pentane-ethyl acetate) affords the desired coupling product. 4.1.2.1.12 (6S,11aR,11bS)-5-(3,4-Dichlorophenyl)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one (2l) Yield: 70%. Orange solid; m.p. 65-68 C; Rf 0.37 (petroleum ether-AcOEt, 70:30); [alpha]D20 – 477 (c = 0.11, CHCl3); 1H NMR (300 MHz, CDCl3): delta = 7.58 (d, J = 2.2 Hz, 1H), 7.46 (d, J = 8.4 Hz, 1H), 7.34 (dd, J = 8.4, 2.2 Hz, 1H), 6.81 (d, J = 1.3 Hz, 1H), 5.62 (s, 1H), 4.27 (d, J = 4.3 Hz, 1H), 2.90-2.84 (m, 1H), 2.63 (dd, J = 9.4, 4.3 Hz, 1H), 2.32-2.23 (m, 1H), 2.18 (dd, J = 11.2, 2.5 Hz, 1H), 1.89-1.82 (m, 2H), 1.68-1.47 (m, 4H), 1.27-1.12 (m, 1H); 13C NMR (75 MHz, CDCl3): delta = 173.5, 169.5, 147.6, 138.3, 133.5, 133.2, 130.8, 128.1, 125.4, 116.5, 105.6, 88.9, 62.9, 61.5, 48.7, 41.7, 27.3, 25.7, 24.0. MS (CI, NH3): m/z = 362 [M+ + H]; HRMS calcd for C19H17Cl2NO2H [M+ + H]: 362.07091; found: 362.07151, error = 1.7 ppm.
The synthetic route of 20555-91-3 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Perez, Marc; Ayad, Tahar; Maillos, Philippe; Poughon, Valerie; Fahy, Jacques; Ratovelomanana-Vidal, Virginie; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 287 – 293;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com