With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.,19311-37-6
4,4?-Di-tert-butyl-2,2?-bipyridine (16.10 mg, 0.06 mmol, 0.6 equiv.) and 1,2-dimethoxyethane -dichloronickel (1:1) (10.99 mg, 0.05 mmol, 0.5 equiv.) were charged under argon in a flask and suspended in dry 1 ,2-dimethoxyethane (10 ml). This mixture was sonicated for 5 mm. In a separated microwave vial under argon Iridium( 1+), [4,4?-bis( 1,1 -dimethylethyl)-2,2?-bipyridine-icNl ,icNl ?]bis [3,5- difluoro-2- [5-(trifluoromethyl)-2-pyridinyl-icN]phenyl-icC] -, (OC-6-3 3)-, hexafluorophosphate( 1-) (1:1) (CAS 870987-63-6) (5.61 mg, 5.00 jimol), N-[5-(7-bromo-4-oxoquinazolin-3(4H)-yl)-2- (trifluoromethoxy)phenyl] -1 -(4-methylpiperazin- 1 -yl)cyclopropanecarboxamide (56.6 mg, 100 jimol),and lithium hydroxide (4.79 mg, 200 jimol) were charged in a 2 mL vial. 1 mL of the nickel pre-catalyst solution was syringed into the vial containing the reaction mixture. The solution was degassed a second time by sparging with argon while stirring for 10 minutes. Under a constant flow of argon, 3- bromotetrahydrofurane (racemate) (14 jil, 150 jimol) and 1,1,1,3,3,3-hexamethyl-2- (trimethylsilyl)trisilane (31 jil, 100 jimol) were added to the reaction mixture using a Hamilton syringe.The reaction mixture was iffadiated with one 34 W blue LED lamp in the EvoluChemTM PhotoChemistry Device using the 8 x 2 mL vial rack which contains an incorportated fan for cooling to maintain the experiment at room temperature. The reaction mixture was then allowed to stir in the device for 15 hours. The reaction mixture was charged completely on a silica gel column and a chromatographic separation was performed with a gradient of dichloromethane/methanol from 100:0 to90:10. The material obtained was purified by preparative RP-HPLC on a 125x30mm column with acetonitrile/water (0.2% ammonia) to provide 10.0 mg (96 % purity, 17 % yield) of the title compound.LC-MS (Method 2): R = 1.88 mm; MS (ESIpos): m/z = 558 [M+H]1HNMR (500 MHz, DMSO-d6) [ppm]: -0.007 (1.09), 0.007 (0.77), 1.106 (1.50), 1.115 (4.03), 1.122 (4.31), 1.129 (1.98), 1.237 (1.98), 1.245 (4.44), 1.251 (3.60), 1.261 (1.50), 1.908 (0.53), 1.968 (0.47),1.983 (1.12), 1.992 (0.62), 1.999 (1.14), 2.008 (1.32), 2.014 (0.54), 2.024 (1.29), 2.039 (0.54), 2.194(16.00), 2.359 (0.43), 2.362 (0.50), 2.366 (0.46), 2.375 (0.89), 2.384 (1.03), 2.391 (1.41), 2.400 (1.97),2.406 (1.52), 2.409 (1.46), 2.415 (2.29), 2.425 (2.09), 2.431 (2.27), 2.453 (4.01), 2.519 (0.66), 2.523(0.54), 3.249 (1.47), 3.265 (1.68), 3.286 (1.08), 3.577 (0.40), 3.592 (1.13), 3.607 (1.72), 3.622 (1.37),3.636 (0.55), 3.651 (2.79), 3.667 (2.88), 3.681 (1.82), 3.813 (1.07), 3.828 (2.52), 3.844 (2.88), 3.859(1.21), 3.981 (1.12), 3.990 (1.19), 3.997 (2.06), 4.007 (2.02), 4.014 (0.95), 4.023 (0.88), 4.079 (2.08),4.094 (2.64), 4.095 (2.57), 4.110 (1.82), 7.374 (2.49), 7.379 (2.51), 7.391 (2.59), 7.396 (2.80), 7.528(2.04), 7.531 (2.08), 7.545 (2.10), 7.548 (2.20), 7.629 (3.95), 7.633 (3.60), 7.677 (1.95), 7.680 (1.86),7.691 (0.78), 7.694 (1.63), 7.697 (1.50), 8.127 (4.08), 8.143 (3.73), 8.352 (9.84), 8.365 (0.76), 8.584(4.25), 8.589 (4.19), 10.650 (3.53).
The synthetic route of 19311-37-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ, NUNEZ, Eloisa; BORISSOFF, Julian; HAHN, Michael; DIETZ, Lisa; ZDENKA, GAUGAZ, Fabienne; BENDER, Eckhard; LANG, Dieter; GIESE, Anja; THEDE, Kai; ZORN, Ludwig; BOULTADAKIS ARAPINIS, Melissa; (190 pag.)WO2019/63708; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem