Reference of 870837-18-6, A common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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.
Synthesis of (Z)-(6S,9aR)-6-(3,4-difluorophenyl)-3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]hexahydropyrido[2,1-c][1,4]oxazin-4-one A solution of (4R,6S)-6-(3,4-difluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one (151 mg) and triphenylphosphonium bromide (220 mg) in acetonitrile (7 mL) was heated under reflux for one hour and then left to cool to room temperature. To the reaction solution, 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (115 mg) and triethylamine (0.22 mL) were added, and the reaction solution was stirred at room temperature for 12 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 150 mg of the title compound. The property values of the compound are as follows. ESI-MS; m/z 466[M++H]. 1H-NMR(CDCl3) delta (ppm): 1.38-1.58(m,2H), 1.66-1.80(m,2H), 2.10-2.28(m,2H), 2.30(s,3H), 3.85(s,3H), 4.03(t,J=10.4 Hz,1H), 4.05-4.16(m,1H), 4.35(dd,J=10.4,2.0 Hz,1H), 5.33(t,J=4.0 Hz,1H), 6.82(s,1H), 6.92(brs,1H), 6.98-7.02(m,1H), 7.04-7.16(m,2H), 7.20(d,J=8.0 Hz,1H), 7.35(d,J=2.0 Hz,1H), 7.36(dd,J=8.0,2.0 Hz,1H), 7.71(d,J=1.2 Hz,1H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/117798; (2007); A1;,
Imidazole – Wikipedia,
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