A common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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. 3469-69-0.
To a solution of 4-iodo-1H-pyrazole (2.0 g, 10.31 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (619 mg, 15.47 mmol) at 0 C. The resulting white suspension was stirred at 0 C for 2 hours. 2-(chloromethoxyethyl)trimethyl silane (SEM-Cl, 90% purity, 2.101 g, 2.230 mL, 11.34 mmol) was added dropwise at 0 C. The suspension was then allowed to warm up to room temperature and stirred for 16 hours. The reaction was quenched with water (0.5 mL), and concentrated to ~5 mL at reduced pressure. The mixture was then partitioned between EtOAc (50 mL) and saturated NaHCC solution (30 mL). The organic layer was separated, washed with brine (20 ml_), dried (Na2S04) and concentrated at reduced pressure. The residue was purified by Biotage Isolera chromatography [SNAP Cartridge KP-Sil 50 g; eluting with a gradient of eluents; 0-20% EtOAc in heptane] to give the title compound (3.27 g, 91% yield) as a colourless oil. 1H NMR (500 MHz, chloroform-d) delta [ppm] 7.62 (s, 1 H), 7.54 (s, 1 H), 5.40 (s, 2H), 3.59 – 3.51 (m, 2H), 0.94 – 0.85 (m, 2H), -0.02 (s, 9H). LCMS (Analytical Method A): Rt = 1.36 mins; MS (ESIPos) m/z = 324.9 (M+H)
The synthetic route of 4-Iodopyrazole has been constantly updated, and we look forward to future research findings.