Application of 89282-03-1 ,Some common heterocyclic compound, 89282-03-1, molecular formula is C5H4INO, its 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.
Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[3,2-c]-2-boronic acid (13): Prepared from 4-hydroxy-3-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 180.7 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder (41%). The mixture was treated with hot EtOH to afford 13 (109.9 mg, 34%) as a paleyellow solid; IR (cm-1) 3000, 1736, 1616, 1591, 1570, 1541, 1473, 1373, 1356, 1300, 1228, 1164, 1145,1039; 1H-NMR (DMSO-d6) delta 7.57 (d, J = 0.5 Hz, 1H), 7.65 (d, J = 6.0 Hz, 1H), 8.46 (d, J = 6.0 Hz, 1H),9.00 (s, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0513 (Delta 0.05).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.
Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem