Adding a certain compound to certain chemical reactions, such as: 33348-34-4, name is 4-Amino-3-iodobenzonitrile, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33348-34-4, Application In Synthesis of 4-Amino-3-iodobenzonitrile
To a 500 mL three-necked round bottom flask containing DMF (195 mL) (deoxygenated with N2 and slight vacuum) were sequentially added 4-amino-3-iodobenzonitrile (12.2 g, 50.0 mmol), pyridine 4-methylbenzenesulfonate (0.477 g, 1.9 mmol), tetraethoxysilane (13.23 g, 63.5 mmol), and ethyl 2-(2-oxocyclopentyl)acetate (12.76 g, 75.0 mmol) under N2. The reaction mixture was heated at 135 C in the dark overnight. To the mixture were added N- ethyl-N-isopropylpropan-2 -amine (26.2 mL, 150 mmol) and palladium (II) acetate (0.337 g, 1.5 mmol) under N2. The resulting mixture was cooled to 120 0C and stirred for additional 16 h. The reaction mixture was cooled to room temperature and acidified to pH ~ 5 with 1 N aq. HCl. The solvent was evaporated under reduced pressure at 60 0C. To the resulting liquid residue was added water (300 mL) and EtOAc (500 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 400 mL). The combined organic layers were dried over Na2SO4, decanted and concentrated under reduced pressure to afford a dark brown liquid (22.1 g). The crude liquid was passed through a silica gel plug and eluted with 10%-40% EtOAc in hexanes. Fractions were concentrated and further purified by precipitation in DCM/hexanes to yield the title compound as a light orange solid (4.65 g). LCMS m/z = 269.2 [M + H]+; 1H NMR (400 MHz, DMSO-J6) delta ppm 1.19 (t, J = 7.12 Hz, 3H), 2.05-2.18 (m, IH), 2.54 (dd, J = 16.44, 8.45 Hz, IH), 2.64-2.85 (m, 4H), 3.52-3.63 (m, IH), 4.12 (q, J = 7.12 Hz, 2H), 7.34 (dd, J = 8.45, 1.58 Hz, IH), 7.49 (d, J = 8.45, IH), 7.85 (d, J = 0.81, IH), 11.30 (s, IH).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Amino-3-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/78983; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com