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1.2.1.2. Illustrative synthesis of Intermediate Gen-3-a: 4-Methyl-3-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2- l)-phenylamine To a suspension, previously degazed with nitrogen bubbling for 1 h, of Intermediate Gen-2-b (300 g, 1.29 mol, 1 eq.), Intermediate Gen-9-a (343.2 g, 1.35 mol, 1.05 eq.) and potassium acetate (380 g, 3.9 mol, 3 eq.) in DMSO (2.65 L), previously degazed with nitrogen bubbling for 2 h, is added PdCl2(dppf).DCM (52 g, 0.06 mol, 0.05 eq.). The reaction mixture is stirred at 80C under nitrogen overnight. The reaction is cooled to room temperature, then water (1.5 L) and EtOAc (3 L) are added. The biphasic solution is filtered through a plug of celite, and the cake is washed with EtOAc (2 L). The two layers of the filtrate are separated, the aqueous layer is extracted again with EtOAc (3 L) and the combined organic layers are washed with water (500 mL). The organic layer is dried over Na2SO i, filtered and evaporated to dryness. The residue is purified by chromatography on silica (elution cyclohexane/EtOAc: 95/5 to 70/30) to afford Intermediate Gen-3-a. lH NMR (300 MHz, CDCl3-i ) delta ppm 7.17 (1 H, d), 6.99 (1 H, d), 6.70 (1 H, dd), 3.54 (2 H, bs), 2.25 (3 H, s), 1.36 (12 H, s)
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; GALAPAGOS NV; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BEAUMONT, Stephane Nicolas Alain; BONNATERRE, Florence Marie-Emilie; WO2015/24905; (2015); A1;,
Iodide – Wikipedia,
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