Some common heterocyclic compound, 191348-14-8, name is 2-Iodo-4-methoxyaniline, molecular formula is C7H8INO, 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. Formula: C7H8INO
A dry flask was charged with 4-methoxy-2-iodoaniline (1.13 g, 4.56 mmol), disilylated alkyne 18 (1.63 g, 5.48 mmol), palladium(II)acetate (101 mg, 0.456 mmol), Na2CO3 (1.43 g, 13.68 mmol) and DMF (12 mL) under argon atmosphere and heated at 90 C for 8 h. DMF and volatiles were removed in vacuo. Ethyl acetate (15 mL) and water (15 mL) were added to the residue. The aqueous phase was extracted with ethyl acetate (3×15 mL). The combined organic extract was washed with 5% NaHCO3 (20 mL) and brine (30 mL), and solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (PE/EtOAc) to give indole 19a (918 mg, 48%) as a light brown oil and 19b (376 mg, 27%) as a light brown sticky material.To a stirred solution of 19b (305 mg, 1 mmol) and imidazole (340 mg, 5 mmol) in DCM (4 mL) was added TESCl (251.7 mL, 1.5 mmol) under argon atmosphere at 0 C. Stirring was continued for another 2 h at 0 C then the reaction was quenched with ice-water, organic part was separated, dried over Na2SO4, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography to give indole 19a (394 mg, 94%) as a light brown oil. Rf=0.52 (PE/EtOAc 25:1). 1H NMR (500 MHz, CDCl3, delta): 7.73 (s, 1H), 7.16 (dd, J=8.5, 2.5 Hz, 1H), 6.97 (d, J=2.0 Hz, 1H), 6.76 (dd, J=8.5, 2.5 Hz, 1H), 3.78 (s, 3H), 3.72 (t, J=7.5 Hz, 3H), 3.00 (t, J=7.5 Hz, 3H), 0.92 (m, 18H), 0.80 (q, J=8.0 Hz, 6H), 0.56 (q, J=8.0 Hz, 6H); IR (neat cm-1): 3398, 2955, 1620, 736; HRMS (ESI): (M+H)+ calcd for +C23H422NO2Si 420.2749, found 420.2748.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 191348-14-8, its application will become more common.
Reference:
Article; Jana, Goutam Kumar; Sinha, Surajit; Tetrahedron; vol. 68; 35; (2012); p. 7155 – 7165;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com