These common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, 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. Product Details of 19718-49-1
Intermediate 1; Methyl 2-(trimethylsilyl)-3-f2-r(trimethylsilyl)oxy1ethyl)-1H-indole-5-carboxylate; Methyl 4-amino-3-iodobenzoate (27.7 g, 0.1 mol), LiCI (4.24 g, 0.1 mol), Cs2CO3 (81.5 g, 0.25 mol), tri(o-tolyl)phosphine (1.52 g, 5 mmol) was added to DMF (500 ml). The mixture was degassed with nitrogen and 4-trimethylsilyl-3-butyn-1-ol (26.67 ml, 0.16 mol) and palladium (II) acetate (1.12 g, 5 mmol) was added, The mixture was degassed with nitrogen and stirred at 100 0C for 3 hours. The reaction mixture was filtered on celite (5 cm) and evaporated. The crude extract was diluted with ethyl acetate, the organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified on SiO2 eluting with dichloromethane/ethyl acetate 95/5 to give a first fraction of the title compound (2.1 g) and a second fraction after evaporation and addition of heptane, precipitation and filtration : (Intermediate 1) (19.3 g, 66 %). LC/MS : m/z 292 (M+H)+, Rt: 2.96
The synthetic route of Methyl 4-amino-3-iodobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (2009); A1;,
Iodide – Wikipedia,
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