Synthetic Route of 620621-48-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 620621-48-9, name is Methyl 2-chloro-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.
Intermediate 77 :methyl 2-chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate; Methyl 2-chloro-5-iodobenzoate (1.00 g, 3.37 mmol), cesium carbonate (1.648 g, 5.06 mmol), BINAP (0.105 g, 0.17 mmol), palladium(II) acetate (0.038 g, 0.17 mmol) and 7V,7V-diethylpyrrolidin-3 -amine (0.576 g, 4.05 mmol) were suspended in dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 120 0C for 2 hours in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite before concentrating in vacuo. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% NH3ZMeOH in DCM. The product was isolated but still contained less polar impurities. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3ZMeOH and pure fractions were evaporated to dryness to afford methyl 2- chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate (0.257 g, 24.52 %) as a brown gum. mZz (ESI+) (M+H)+ =311; HPLC tR = 1.16 min. 1H NMR (400.13 MHz, DMSO-d6) delta 0.96 (6H, t), 1.80 – 1.85 (IH, m), 2.11 – 2.17 (IH, m), 2.54 – 2.63 (4H, m), 2.99 (IH, t), 3.15 – 3.22 (2H, m), 3.40 – 3.44 (2H, m), 6.53 – 6.56 (2H, m), 7.16 – 7.18 (IH, m), 7.42 (IH, s), 7.67 (IH, s).
The chemical industry reduces the impact on the environment during synthesis Methyl 2-chloro-5-iodobenzoate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
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