Category: 672293-33-3

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

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 672293-33-3, name is Methyl 4-amino-5-iodo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-5-iodo-2-methylbenzoate

To a solution of methyl 4-amino-5-iodo-2-methylbenzoate 2 (0.84 g, 2.90 mmol, 1 eq.) in DMF (10 mL), 2-oxobutyric acid (1.48 g, 14.5 mmol, 5 eq.) and DABCO (0.975 g, 8.7 mmol, 3 eq.) were added. The solution was stirred for 5 min and then palladium (II) diacetate (0.03 g, 0.145 mmol, 0.05 eq.) was added. The mixture was warmed to 105C, stirred during 16 h and then concentrated. The resulting solid was dissolved in AcOEt (150 mL) and washed with water (150 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuuo to obtain dark brown solid which was purified by trituration in AcOEt to give the desired indole 6 as grey powder (358 mg, 1.45 mmol, 50%); Mp : 280-282C (Dec.); Rf = 0.61 (SiO2, Cyc/AcOEt, 5/5); 1H NMR (400 MHz, CD3OD) 8.30 (s, 1H, H-4), 7.25 (s, 1H, H-7), 3.99 (s, 3H, CH3), 2.65 (s, 3H, CH3), 2.59 (s, 3H, CH3); 13C NMR (100 MHz, CD3OD) 168.1 (C=O), 165.3 (C=O), 139.6 (C), 137.2 (C), 128.0 (C), 127.7 (C), 125.6 (CH), 122.3 (C), 118.9 (C), 114.8 (CH), 52.1 (CH3), 22.9 (CH3), 9.94 (CH3); HR-ESIMS: [M-H]- m/z calcd for C13H12NO4 246.0766 found 246.0777.

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:
Article; Vogrig, Alexandre; Boucherle, Benjamin; Deokar, Hemantkumar; Thomas, Isabelle; Ripoche, Isabelle; Lian, Lu-Yun; Ducki, Sylvie; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3349 – 3353;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 672293-33-3, 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.

A solution of NaNO2 (5.33 g, 77.25 mmol) in water (150 mL) was added dropwise to a solution of 18A (15.0 g, 51.53 mmol) in conc. HCl (150 mL) at -5 C. over a period of 20 min. The reaction mixture was stirred at -5 C. for 1 hour, then a solution of CuCl (7.72 g, 0.078 mmol) in conc. HCl (150 mL) was added. The reaction mixture was stirred at 60 C. for 4 hours. After cooling, the resulting mixture was extracted with EtOAc (400 mL¡Á3). The combined organic fractions were washed with water and brine and dried over sodium sulfate. The solvent was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (4% EtOAc in pet. ether) to provide 18B (9.69 g, 60% yield) as yellow oil: ESI m/z 311, 313.0 [M+H]+.

Statistics shows that Methyl 4-amino-5-iodo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 672293-33-3.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com