Synthetic Route of 101417-40-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 101417-40-7, name is 4-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide (0.050 g, 0.136 mmol) in anhydrous dimethylformamide (3 mL) in a flamed dried flask under argon atmosphere at 0 C. was added sodium hydride (60% in mineral oil, 0.014 g, 0.339 mmol) was added in one portion. The reaction was stirred for 10 min at 0 C. then 4-(bromomethyl)benzo[d][1,3]diozole (0.031 g, 0.142 mmol) was added as a solid in one portion. The mixture was stirred for 90 minutes, then 1 hour at room temperature. After consumption of starting material, the reaction mixture was quenched with saturated ammonium chloride (25 mL) and extracted with ethyl acetate (2*25 mL). The combined organics were washed once with saturated sodium bicarbonate (50 mL) and dried over anhydrous sodium sulfate. The concentrated residue was purified by flash chromatography over silica gel using 95:5 dichloromethane/methanol to give N-(4-(1-(benzo[d][1,3]dioxol-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-2,4-dimethyloxazole-5-carboxamide (0.063 g, 92%) as light yellow solid. 1H NMR (400 MHz, DMSO-d): delta 12.52 (s, 1H), 7.80 (d, 1H, J=1.6 Hz), 7.70 (dd, 1H, J=8.4, 2.0 Hz), 7.56 (bs, 1H), 6.97 (d, 1H, J=8.4 Hz), 6.80 (dd, 1H, J=8.0, 1.6 Hz), 6.75 (m, 1H), 6.59 (dd, 1H, J=8.0, 1.6 Hz), 6.05 (s, 2H), 5.10 (s, 2H), 2.99 (m, 2H), 2.71 (m, 2H), 2.48 (s, 3H), 2.40 (s, 3H). MS (ESI): Calcd. for C26H22N4O5S: 502, found 503 (M+1)+.
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, 4-(Bromomethyl)benzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary