Application of 6940-76-7, 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. 6940-76-7 name is 1-Chloro-3-iodopropane, 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.
To a solution of TMEDA (4.36 mL, 28.9 mmol) in THF (30 mL) at -20 C was added n- butyllithium (12.03 mL, 28.9 mmol, 2.4 M solution in hexanes) over ten minutes. The mixture was stirred at 10 C for 30 minutes, then cooled to -78 C, and a solution of tert- butyl (6-chloropyridin-2-yl)carbamate (3 g, 13.12 mmol) in THF (15 mL) was added over a period of 5 minutes. After 40 minutes, copper(I) iodide (2.499 g, 13.12 mmol) was added, and the mixture was stirred at -10 C for 1 hour. l-Chloro-3-iodopropane (2.113 mL, 19.68 mmol) was added over a period of 1 minute, and the mixture was allowed to reach room temperature. After 2.5 hours the mixture was added to saturated aqueous sodium hydrogencarbonate and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was stirred in dichlorom ethane (30 mL), filtered through a glass- sintered funnel and concentrated to half volume and then applied onto a flash column (120 g silica), eluting with 2-20% ethyl acetate in heptane. The eluent coming off the column was passed through a column of potassium carbonate. This gave the desired product tert-butyl 7- chloro-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate (2.637 g). Yield 74% NMR (400 MHz, Chlorofomwf) d 7.32 (d, J = 7.9 Hz, 1H), 6.94 (d, J = 7.8 Hz, 1H), 3.81 – 3.69 (m, 2H), 2.73 (t, J= 6.6 Hz, 2H), 1.93 (p, J= 6.5 Hz, 2H), 1.54 (s, 9H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-3-iodopropane, and friends who are interested can also refer to it.
Reference:
Patent; MORPHIC THERAPEUTIC, INC.; HARRISON, Bryce, A.; DOWLING, James, E.; GERASYUTO, Aleksey, I.; BURSAVICH, Matthew, G.; TROAST, Dawn, M.; LIPPA, Blaise, S.; ROGERS, Bruce, N.; ZHONG, Cheng; QIAO, Qi; LIN, Fu-Yang; SOSA, Brian; BORTOLATO, Andrea; SVENSSON, Mats, A.; HICKEY, Eugene; KONZE, Kyle, D.; DAY, Tyler; KIM, Byungchan; (124 pag.)WO2020/47208; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com