Category: 20816-79-9

Synthetic Route of 20816-79-9, A common heterocyclic compound, 20816-79-9, name is 1-Bromo-8-chloronaphthalene, molecular formula is C10H6BrCl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of benzyl (2S)-2-(cyanomethyl)-4-[2-[[(2,S)-l – methylpyrrolidin-2-yl]methoxy]-6,7,8,9-tetrahydro-5/7-pyrimido[4,5-c]azepin-4-yl]piperazine-l – carboxylate (250 mg. 481 pmol, 1.0 eq) and l-bromo-8-chloro- naphthalene (232 mg, 962 pmol, 2.0 eq) in toluene (4.0 mL) was added RuPhos (89.8 mg, 192 pmol, 0.4 eq), CS2CO3 (392 mg, 1.20 mmol, 2.5 eq) and Pd2(dba)3 (88.1 mg, 96.2 pmol, 0.2 eq), the reaction mixture was stirred at 90 C for 10 hours under N2. After completion, the reaction mixture was filtered through a celite, the filter cake was washed with ethyl acetate (10 mL), and adjusted with 1N HC1 aqueous to pH~3, the organic layer was separated, and the aqueous was adjusted with Na2C03 solid to pi 1 8. extracted with ethyl acetate (2 x 10 mL), the organic layer was washed with saturated brine (1 c 20 mL), dried over Na2S04, filtered and concentrated. The residue was purified by reverse phase flash (Cl 8, 0.1 %FA in water, 30%-50% MeCN). The product benzyl (25 -4-[8-(8- chloro-l-naphthyl)-2-[[(25)-l -methylpyrrolidin-2-yl] methoxy]-5,6,7,9-tetrahydropyrimido[4,5- c]azepin-4-yl]-2-(cyanomethyl)piperazine-l-carboxylate (130 mg, 185 pmol, 38% yield, 97% purity) was obtained as yellow solid. LCMS [ES1, M+l]: 680. (0587) [0348] NMR (400 MHz, chloroform-d) d 7.74 – 7.68 (m, 1H), 7.59 – 7.51 (m, 1H), 7.48 – 7.15 (m, 9H), 5.21 (s, 2H), 4.74 – 4.63 (m, 1H), 4.40 – 4.29 (m, 211), 4.21 – 4.05 (m, 211), 3.84 – 3.71 (m, 1 H), 3.69 – 3.46 (m, 2H), 3.44 – 3.15 (m, 3LI), 3.13 – 2.60 (m, 8H), 2.46 (s, 3H), 2.33 – 2.21 (m, 1 H), 2.17 – 2.02 (m, 2H), 1.96 – 1.72 (m, 4H). LCMS [ESI, M+l]: 546.

The synthetic route of 20816-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; MARX, Matthew, Arnold; BLAKE, James, F.; FELL, Jay, Bradford; FISCHER, John, P.; MEJIA, Macedonio, J.; (164 pag.)WO2020/47192; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 20816-79-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20816-79-9, name is 1-Bromo-8-chloronaphthalene, This compound has unique chemical properties. The synthetic route is as follows.

Under a nitrogen atmosphere,the intermediate A-BE, 1-bromo-8-chloronaphthalene, and potassium carbonate were mixed at a molar ratio of 1: (1.0-1.2):3.0 under a nitrogen atmosphere, and added to the catalyst containing palladium acetate and tri-tert-butylphosphine tetrafluoroboratein toluene/water,Under reflux with nitrogen for 12-16h, cooled down, the reaction solution is allowed to stand for liquid separation, dried, and purified by column chromatography to obtain intermediate M-1.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-8-chloronaphthalene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Li Qing; Li Zishu; Shi Yu; Meng Fanmin; Zhou Yinbo; Hu Baohua; (17 pag.)CN108586319; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics