Synthetic Route of 910251-11-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 910251-11-5 name is Potassium trifluoro(methoxymethyl)borate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
4-Chloro-2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]quinazoline-7-carboxamide (200 mg, 0.0005 mol)(INT-5 described in Example 7), potassiummethoxymethyltrifluoroborate (214 mg, 0.00141 mol) dicesium carbonate (458 mg, 0.00141 mol) and SiliaCat DPP-Pd(0.260 mmol/g loading; 361 mg, 0.0000938 mol) were weighed into a 2-5mL microwave vial purged with nitrogen 5 min then added 1,4-dioxane (7.65 mL, 0.0980 mol) and water (1.69 mL, 0.0938 mol). The mixture was heated at 155 C for 80 min under microwave irradiation. After cooling, the reaction mixture was poured into EtOAc and water. The layers were separated and the aqueous layer was extracted two more times with EtOAc. The combined organic layer was dried over anhydrous MgSC>4 and concentrated in vacuo, and purified by HPLC to give 2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]-4- (methoxymethyl)quinazoline-7-carboxamide (20.0 mg, 10%) as a white solid. LCMS (ESI+): m/z = 436.2 (M+H). lH NMR (400 MHz, DMSO-dg) delta 9.12 (s, 1H), 8.63 – 8.56 (m, 3H), 8.45 (d, J= 8.6 Hz, 1H), 8.16 (s, 1H), 8.13 (d, J= 8.7 Hz, 1H), 7.68 (d, J= 8.6 Hz, 2H), 6.91 (s, 2H), 5.13 (s, 2H), 3.48 (s, 3H), 3.32-3.44 (m, 2H), 2.73 (t, J = 7.5 Hz, 2H), 2.01 – 1.93 (m, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium trifluoro(methoxymethyl)borate, and friends who are interested can also refer to it.
Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; FREEZE, Brian, Scott; GIGSTAD, Kenneth, M.; JANOWICK, David, A.; LEE, Hong, Myung; SHI, Zhan; SOUCY, Francois; VYSKOCIL, Stepan; (237 pag.)WO2016/118565; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem