Tag: M.W=200-300

Electric Literature of 612-55-5,Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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.

In an open vial with pressure-release top, a stirred mixture of 2- iodonaphthylene (Aldrich, St. Louis, MO) (64 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and ira/i5,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred for 6 hours. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtOAc (20 mL), filtered through Celite and the filter cake washed with EtOAc (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (2 prep TLC plates used) using EtOAc / hexane (1:99) as eluent to give the product (46.2 mg, 78%) as a solid.[00215] Data identical to above in Example 5.

The synthetic route of 612-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Standard procedure: Into a flask of 150 mL of EtiO at -78 C under N2, 4-bromo-1-iodo-2-methylbenzene (22.6 g, 76.1 mmol) in anhydrous EtiO (10 mL) is added.. Then n-BuLi in hexanes (2.5 M, 26 mL, 65 mmol) is added dropwise at -78 C and stirred for an additional hour. Then, freshly prepared crude (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde (12.0 g, 21.7 mmol) dissolved in E20 (90 mL) is added via cannula over a period of 5 minutes. The mixture is stirred at -78 C for 30 min, and then slowly warmed to 0 C over a period of 1.5 h. The reaction mixture is quenched with saturated aq. NLLCl and extracted with EtOAc (250 mL x 3). The combined organic phase is washed with brine (100 mL), dried over NaiSOr and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel chromatography DCM/EtO Ac/petroleum ether to give (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (4.0 g, 25% yield for two steps) as a light yellow oil and (S)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (8.0 g, 51 % yield for two steps) as a light yellow oil. (R) isomer: Formula: C42H43Br06 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for 1 R: NMK (300 MHz, CDCl3) d 7.41-7.28 (m, 21H), 7.18-7.13 (m, 2H), 5.08 (d,.7= 5.1Hz, 1H), 4.71 (d, J= 11.7 Hz, 1H), 4.64-4.56 (m, 3H), 4.49 (s, 2H), 4.40 (s, 2H), 4.28 – 4.21 (m, 1H), 4.18 – 4.13 (m, 1H), 4.10 (t, J= 5.1Hz, 1H), 3.99-3.94 (m, 1H), 3.89 (t, J= 5.9 Hz, 1H), 3.83-3.70 (m, 2H), 3.49 (br. s., 1H), 2.29 (s, 3H). ESI-MS [M+Na+] calcd for (CriH-nB ENa) found: 745.5 (100%), 747.5 (97.3%) (S) isomer: Formula: C42H43BrC>6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for IS: 1H NMR (300 MHz, CDCl3) d 7.37 – 7.16 (m, 23H), 5.06 (d, J= 5.5 Hz, 1H), 4.73 – 4.67 (m, 1H), 4.62 – 4.44 (m, 7H), 4.11 – 4.03 (m, 2H), 3.85 – 3.76 (m, 3H), 3.73 – 3.67 (m, 2H), 3.19 (br. s., 1H), 2.18 (s, 3H). ESI-MS [M+Na]+ calcd for C42H43BrOeNa+ 745.21, found 745.5 (100%), 747.5 (97.3%).

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, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FIMBRION THERAPEUTICS, INC.; BISHOP, Michael Joseph; COLANDREA, Vincent J.; LI, Yuehu; STEWART, Eugene L.; STRAMBEANU, Iulia; WIDDOWSON, Katherine Louisa; JANETKA, James Walter; MCGRANE, Laurel Kathryn; (0 pag.)WO2020/12336; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., name: 5-Fluoro-2-iodobenzoic acid

Example 6 [00628] Preparation of Cpd 65 [00629] Step A: A mixture of 5-fluoro-2-iodobenzoic acid (9.04 g, 34.0 mmol), but-3-yn-2-ol (5.7 mL, 5.46 g, 78.0 mmol), ZnCl2 (4.62 g, 34.0 mmol), Pd(Ph3P)4 (1.96 g, 1.7 mmol), Et3N (14.2 mL, 10.3 g, 102.0 mmol) and DMF (50 mL) was stirred under argon at 100 C for 2 hours. After the removal of the volatiles under vacuum, the residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-50%) to provide intermediate 7-fluoro-3-(l-hydroxyethyl)-lH- isochromen-l-one as a brown oil (5.93 g, 84%). MS m/z 209.2 [M+H]+; 1H NMR (500 MHz, CDCl3-

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; PTC THERAPEUTICS, INC.; CHEN, Guangming; DAKKA, Amal; KARP, Gary Mitchell; LI, Chunshi; NARASIMHAN, Jana; NARYSHKIN, Nikolai; WEETALL, Maria L.; WELCH, Ellen; ZHAO, Xin; WO2013/112788; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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. Safety of 4-Iodo-2-methylaniline

Compound E (e.g., 4.3mmol) was added in ethyl acetate (e.g., 30mL), water (e.g., 30mL) and sodium hydroxide (e.g., 4.8mmol) were added and the resulting product was used for the subsequent reaction. 2, 2, 2-trichloroethyl chloroformate (e.g., 4.7mmol) was added dropwise to the above solution at 0-5C .Aftercompletionofdropping, the reaction was carried out at room temperature for 1 hour. The organic phase was separated, dried and concentrated under reduced pressure to obtain compound F, the yield was >95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13194-68-8, its application will become more common.

Reference:
Patent; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; SHI, Ying; MI, Yi; YANG, Hanyu; WANG, Xuliang; GONG, Denghuang; BAI, Min; CHEN, Xiaozhuo; CHEN, Yujie; ZHANG, Xuejiao; MA, Yuxiu; GAO, Qingzhi; (77 pag.)EP3357916; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 90347-66-3

Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4′,4′,5,5,5′,5,-octamethyl-2,2′-bi(l ,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCl2(dppf CH2Cl2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous NaHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71 %). NMR (400 MHz, CDC13) 5 8.41 (d, J = 1.9 Hz, 1 H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 35674-27-2,Some common heterocyclic compound, 35674-27-2, name is 4-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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.

Example 2 Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Trimethyl Orthoacetate A solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in trimethyl orthoacetate (30 ml) is refluxed (?110 C.) for 15 hours and then solvent is evaporated under reduced pressure. The 4-iodo-3-nitrobenzoic acid methyl ester is obtained as a yellow solid (3.11 g, 99% yield, 97.5% HPLC).

The synthetic route of 35674-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIVI’S LABORATORIES LIMITED; Divi, Murali Krishna Prasad; Rao, Mysore Aswatha Narayana; Rajuri, Venkataramana; US2013/172618; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, A new synthetic method of this compound is introduced below., SDS of cas: 460-37-7

General procedure: 500 mg (2.00 mmol) of the compound from Ex. 31A and 690 mg (5.00 mmol) of potassium carbonate were stirred in 10 ml of anhydrous DMF at RT for 15 min, before 449 mul (4.00 mmol) of (bromomethyl)cyclobutane were added. Then the reaction mixture was stirred at 50 C. for about 16 h. After cooling to RT, water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The product was isolated by means of MPLC (Biotage Isolera One, SNAP KP-Sil cartridge, 50 g of silica gel, eluent: cyclohexane/ethyl acetate 2:1). After concentration of the product fractions and drying under high vacuum, 486 mg (76% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 10.07 (s, 1H), 3.96 (d, 2H), 2.82-2.69 (m, 1H), 2.76 (s, 3H), 2.66-2.58 (m, 1H), 2.04-1.91 (m, 2H), 1.89-1.74 (m, 4H), 1.07-0.96 (m, 2H), 0.73-0.64 (m, 2H). LC/MS (Method 1, ESIpos): Rt=1.89 min, m/z=319.11 [M+H]+.

The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; HAERTER, Michael; KOSEMUND, Dirk; CANCHO GRANDE, Yolanda; DELBECK, Martina; KALTHOF, Bernd; LUSTIG, Klemens; SUESSMEIER, Frank; US2020/16159; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 146137-72-6, name is 2-Fluoro-6-iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Fluoro-6-iodobenzaldehyde

General procedure: A mixture of 2-ethynylbenzaldehyde (12a) (1.00 g, 7.68 mmol), 1-bromo-2-iodo-benzene (13a) (1.18 mL, 9.22 mmol), CuI (146 mg, 0.77 mmol), PdCl2(PPh3)2 (107 mg, 0.15 mmol), and Et3N (15 mL) in THF (15 mL) was stirred at 80 C for 2 h under argon, and filtrated through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography over silica gel with hexane-EtOAc (15:1).

The synthetic route of 146137-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tokimizu, Yusuke; Ohta, Yusuke; Chiba, Hiroaki; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki; Tetrahedron; vol. 67; 29; (2011); p. 5168 – 5175;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 3210-08-0, name is 4-Iodobutan-1-ol, A new synthetic method of this compound is introduced below., Recommanded Product: 3210-08-0

To a solution of 5-iodobutan-1-ol (16.5 g, 82.5 mmol, 1 equiv) in dryDMSO (75 mL), solid NaCN (6.06 g, 124 mmol, 1.5 equiv) was added in small portions at0 C. The reaction progress was surveilled by NMR spectroscopy. It is instant and the titlecompound as well as THF (6 : 5) are formed. After complete conversion, the reaction mixturewas diluted with water (75 mL) and extracted with Et2O (5 ¡Á 100 mL). The combined organiclayers were washed with brine and dried over Na2SO4. Evaporation of the solvent yielded thetitle compound in pure form.

The synthetic route of 3210-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wuensch, Matthias; Schroeder, David; Froehr, Tanja; Teichmann, Lisa; Hedwig, Sebastian; Janson, Nils; Belu, Clara; Simon, Jasmin; Heidemeyer, Shari; Holtkamp, Philipp; Rudlof, Jens; Klemme, Lennard; Hinzmann, Alessa; Neumann, Beate; Stammler, Hans-Georg; Sewald, Norbert; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2428 – 2441;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-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 77317-55-6, Computed Properties of C8H8INO2

To a solution of methyl anthranilate (7.75 g, 51.3 mmol, Aldrich) in DMF [(50] [ML)] was added NIS (11. [5] g, [51.] 3 mmol, Aldrich). The solution was stirred for 63 hours before being added to a separatory funnel with 200 mL of MTBE and washed with 5 X 200 mL of water. The organics were dried over MgS04 and evaporated yielding 13.8 g of tan solid as methyl [2-AMINO-5-IODOBENZOATE.] A mixture of methyl 2-amino-5- iodobenzoate (3.13 g, 11.3 mmol) and tetrakis (triphenylphosphine) palladium [(0)] (282 mg, 0.244 mmol, Strem) was placed under 1 atm of CO. THF (20 mL) was added, [ANDTHE SOLUTIONWAS HEATEDTO 60 C. TRI-N-BUTYLTINHYDRIDE] (3.7 mL, 12.7 mmol, Aldrich) was added dropwise with rapid stirring over 4 hours. The dark orange solution was heated a further 45 minutes and then added to a separatory funnel with [150] mL of EtOAc. This solution was washed with 2 X [150] mL of saturated aqueous NaHCO3 followed by 100 mL of brine. It was dried over MgS04 and evaporated leaving a brown oil that was purified by chromatography using a Biotage Flash 40 M silica cartridge with a gradient from [CHUCK] to 5% EtOAc in [CHZCLZ] as eluent. This chromatography failed to remove all of the tin, so the product was re- chromatographed using a Biotage Flash 40 M silica cartridge with 5% EtOAc in [CHUCK] as eluent. Yield was 863 mg of white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com