These common heterocyclic compound, 672293-33-3, name is Methyl 4-amino-5-iodo-2-methylbenzoate, 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. COA of Formula: C9H10INO2
[0069] Methyl (2-(l-oxopeutyl)-3-(2-phenylethyl)-6-methyl)indole-5-carboxyIate (7); Amixture of 4 (250 mg), l-triethylsilyl-4-phenylbutyne (5, 320 mg), palladium acetate (30 mg), sodium carbonate (450 mg), and degassed DMF (2 mL) was stirred at 100C under argon atmosphere for 5 hours. The reaction mixture was filtered through fluorisil, eluted with 20% ethyl acetate/hexanes and evaporated to afford indole 6 as an amorphous. To a mixture of 6, dichloromethane (3 mL) and valeryl chloride (0.52 mL), zinc chloride (1M in diethyl ether solution, 0.77 mL) was added slowly at 4C, and stirred at 4C for 3 hours. The reaction mixture was treated with methanol (3 mL), diluted with ethyl acetate (30 mL), washed with water twice (10 mL each), aqueous sodium carbonate (10 mL) followed by brine (10 mL), dried (Na2S04), and evaporated. The crude residue was washed with hexanes to give 7 (165 mg) as a brown solid. Mp 145-147C; ]H NMR (CDC13, 400 MHz) 8 8.87 (s, 1H), 8.32 (s, 1H), 7.30-7.20 (m, 3H), 7.19 (s, 1H), 7.14 (d, J= 7.6 Hz, 2H), 3.93 (s, 3H), 3.39 (t, J= 8.4 Hz, 2H), 3.01 (t, J= 7.2 Hz, 2H), 2.74 (t, J= 7.6 Hz, 2H), 2.71 (s, 3H), 1.68 (quintet, J= 7.6 Hz, 2H), 1.68 (dt, J= 7.6 Hz, 15.2 Hz, 2H), 0.95 (t, J= 7.2 Hz, 3H).
The synthetic route of Methyl 4-amino-5-iodo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/7542; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com