Author: Jessica.F

Some common heterocyclic compound, 761426-65-7, name is 2-Cyclopropyl-5-iodo-1H-imidazole, molecular formula is C21H29N3O6, 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. 761426-65-7

Example 8 (E-8, Co. No. 25) Pd(PPh3)4 (23.2 mg, 20.1 mmol) was added to a stirred suspension of I-20b (150 mg, – 0.40 mmol) and 2-cyclopropyl-5-iodo-lH-imidazole (112.8 mg, 0.48 mmol) in a sat. sol. of NaHC03 (2 mL) and 1,4-dioxane (1 mL). The mixture was stirred at 120 C for 10 min under microwave irradiation. The mixture was concentrated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH/ DCM 0/100 to 6/94). The desired fractions were collected and evaporated in vacuo. The product was purified by RP HPLC (Stationary phase: C18 XBridge 30 x 100 mm 5 muiotaeta; mobile phase: gradient from 60% 0.1 %> NH4C03H/NH4OH pH 9 solution in water, 40% CH3CN to 43% 0.1% NH4C03H/NH4OH pH 9 solution in water, 57% CH3CN) , to yield Co. No. 25 (90 mg, 51%) as a light yellow fluffy solid. 1H NMR (400 MHz, CDC13) delta ppm 0.91 – 1.02 (m, 4 H) 1.72 (d, J=6.7 Hz, 3 H) 1.90 – 2.00 (m, 1 H) 3.98 (dd, J=12.5, 7.4 Hz, 1 H) 4.24 (dd, J=12.7, 4.2 Hz, 1 H) 4.68 – 4.79 (m, 1 H) 7.28 (s, 1 H) 7.42 (dd, J=8.3, 1.4 Hz, 1 H) 7.60 (d, J=2.1 Hz, 1 H) 7.82 (d, J=8.6 Hz, 1 H) 7.88 (s, 1 H) 11.88 (br s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 761426-65-7, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN GOOL, Michiel, Luc, Maria; ALCAZAR-VACA, Manuel, Jesus; ALONSO-DE DIEGO, Sergio-Alvar; DE LUCAS OLIVARES, Ana, Isabel; (105 pag.)WO2016/87487; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

32673-41-9, A common compound: 32673-41-9, name is 4-Imidazolemethanol hydrochloride, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 29 5-chloro-N-((1-(3-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (40) A mixture of 2,5-diiodofluorobenzene II-4 (2.50 g, 7.18 mmol), 4-hydroxymethylimidazole hydrochloride (0.967 g, 7.18 mmol), 8-hydroxyquinoline (0.104 g, 0.717 mmol) and K2CO3 (2.00 g, 14.5 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (0.136 g, 0.716 mmol). The mixture in a sealed tube was heated at 130 C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with MeOH in CH2Cl2 (0-5% MeOH) to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g).

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-Imidazolemethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-87-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below.

[0395] Under inert atmosphere, a mixture of Example 43f (100 mg, 0.27 mmol), Example 43g (144 mg, 0.69 mmol), Pd(PPh3)2Cl2 (19 mg, 0.027 mmol), triethylamine (272 mg, 2.7 mmol) and Cul (5.2 mg, 0.027 mmol) in 10 mL of DMF was stirred at 80C for 2 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by Prep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 mum,, speed: 80 mL/min, eluent: H20/CH3CN = from 80/20 to 20/80 over 50 min)to give the desired product (17 mg, yield: 14.2%) as a yellow solid. LCMS [M+l] +=444.0 [0396] 1H NMR (400 MHz, DMSO-d6) delta 10.85 (s, 1H), 8.85 (s, 1H), 8.19 (d, J= 8.3 Hz, 1H), 8.02 (t, J= 8.0 Hz, 1H), 7.89 (d, J= 7.6 Hz, 1H), 7.77 (d, J= 7.1Hz, 1H), 7.68 (s, 1H), 7.57 (s, 1H), 7.38 (d, J=11.1Hz, 1H), 5.72 – 5.61 (m, 1H), 3.67 (s, 3H), 3.32 (s, 3H), 1.42 (d, J= 6.6 Hz, 6H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem