Adding a certain compound to certain chemical reactions, such as: 89901-03-1, name is Methyl 4′-bromo-[1,1′-biphenyl]-4-carboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 89901-03-1, SDS of cas: 89901-03-1
To a round bottom flask was added methyl 4′-bromobiphenyl-4- carboxylate (2.0 g, 6.87 mmol, 1 .0 equiv) followed by a solution of racemic 2-trans- ethynylcyclopropyl)methanol (0.991 g, 10.30 mmol, 1.5 equiv) dissolved in THF (20 ml_). To this was added palladium dichloride bis-triphenylphosphine (241 mg, 0.343 mmol, 0.05 equiv), copper(l) iodide (131 mg, 0.687 mmol, 0.1 equiv), then triethylamine (6.87 ml_, 49.3 mmol, 7.18 equiv). The reaction was stirred at 75C for ~2 h. The reaction was cooled to room temperature, the solids filtered off, rinsing with THF. The solution was placed in the freezer for 5 days. Concentrate down to dryness. Add DCM and a precipitate forms. Filter precipitate, rinse with minimal DCM. TLC shows ppt contains mostly product (~1.5g solid). Triturate with 10%EtOAc in hexanes (5 mL), pipet off solvent, TLC shows solid contains product and liquid removed starting material-bromide and some baseline impurities. Additional 10%EtOAc in hexanes (5 mL) was added and stirred for 30 minutes, filtered, rinsed with 10%EtOAc in hexanes (5mL), and dried solid. Yielded 900 mg crude methyl 4′-(((1 ,2-irans)-2- (hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-carboxylate. 1 H NMR (DMSO-d6): delta 0.82-0.85 (m, 2H), 1.35-1.43 (m, 2H), 3.23-3.29 (m, 1 H), 3.40-3.42 (m, 1 H), 3.84 (s, 3H), 4.65-4.67 (t, 1 H), 7.43-7.45 (d, 2H), 7.67-7.70 (d, 2H), 7.80-7.82 (d, 2H), 7.99- 8.01 (d, 2H)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4′-bromo-[1,1′-biphenyl]-4-carboxylate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ACHAOGEN, INC.; KASAR, Ramesh; LINSELL, Martin Sheringham; AGGEN, James Bradley; LU, Qing (Jane); WANG, Dan; CHURCH, Tim; MOSER, Heinz E.; PATTEN, Phillip A.; WO2012/154204; (2012); A1;,
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