Category: 82998-57-0

82998-57-0, Name is 3-Iodo-4-methylbenzoic acid, 82998-57-0, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Example 52; 3-r8-r2,6-difluorophenvn-2-r4-methyl-L4′-birhoirhoeridin-l’-v?-7-oxo-7,8- dihvdropyridor2,3-ff1pyrimidin-4-yll-4-methylbenzoic acidTo a stirring solution of 3-iodo-4-methylbenzoic acid (60 g, 0.22 mol, 1 eq) in degassed DMF (1400 mL, 23.3 vol.) was charged 4,4,4′,4′,5,5,5′,5′-octamethyl- 2,2′-bi-l ,3,2-dioxaborolane (81.4 g, 0.32 mol, 1.4 eq) followed by potassium acetate (112 g, 1.14 mole, 5eq) and [l,r-bis(diphenylphosphino)ferrocene]- dichloropalladium(II) (18.7 g, 0.02 mole, 0.1 eq). The resulting mixture was placed under a nitrogen atmosphere and was heated to 80 0C with the exclusion of light overnight. The mixture was then concentrated under high vacuum and the residue partitioned between EtOAc and 2M HCl. The mixture was then filtered and the layers separated. The aqueous phase was re-extracted with EtOAc. The combined EPO organics were then washed with brine, dried and evaporated to yield a brown solid that was applied to a silica plug then eluted with 2:1 cyclohexane : ethyl acetate. Fractions were then combined and evaporated to yield a brown foam that was triturated with cyclohexane, collected by filtration then dried in vacuo to yield A- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid, delta (CDCl3) 8.50- 8.49 (IH, d), 8.04-8.02 (IH, dd), 7.27-7.25 (IH, d), 2.61 (3H, s), 1.36 (12H, s).To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(4-methyl-l,4′- bipiperidin-r-yl)pyrido[2,3-?f|pyrimidin-7(8H)-one (47.5 mg, 0.1 mmol) in dioxane (3 niL) and water (1 mL) were added 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoic acid (38.4 mg, 0.15 mol), potassium carbonate (83 mg, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.6 mL, 0.005 mmol). The mixture was heated with microwave at about 1500C for about 15 min. The mixture was concentrated & then mixed with DMSO (0.75 mL) and water (0.25 mL). Separation by EtaPLC afforded the title compound (39 mg, 68%). LC-MS m/z 574 (M+Eta)+.

Statistics shows that 3-Iodo-4-methylbenzoic acid is playing an increasingly important role. we look forward to future research findings about 82998-57-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/104917; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, name is 3-Iodo-4-methylbenzoic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 82998-57-0

3-Iodo-4-methylbenzoic acid (lOg, 38.16mmol), bis (pinnacolato) diboron (14.5g, 57. 24mmol), potassium acetate (18.73g, 190.8mmol) and PdCl2dppf (3.12g, 3.8mmol) in DMF (200ml) were heated at 80C for 21hrs. The solvent was evaporated from the cooled reaction under vacuum, the residue dissolved in ethyl acetate (300ml) and hydrochloric acid (2N, 300ml) and filtered through celite. The organic phase was separated and the aqueous extracted with ethyl acetate (2 x 300ml). The combined organic extracts were washed with brine (500ml) and dried (magnesium sulphate). The solvent was evaporated under vacuum and the residue was absorbed onto silica and applied to a silica column. This was eluted with cyclohexane/ethyl acetate (5: 1). to give the title compound. NMR: AH [d6-DMSO] 12.83, (1H, b), 8.23, (1H, d), 7.89, (1H, dd), 7.29, (1H, d), 2.51, (3H, s), 1.30, (12H, s). LCMS: Rt 3. 65min.

Statistics shows that 82998-57-0 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-4-methylbenzoic acid.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/10995; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0,Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, molecular formula is C8H7IO2, 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.

3-Iodo-4-methyl benzoic acid (200 mg, 0.763 mmol) and thionyl chloride (4.5 mL, 612 mmol) were heated to 80 C. in a round-bottom flask equipped with a reflux condenser for 1 hr. After cooling to room temperature, the reaction mixture was concentrated on the rotary evaporator and then high vacuum for 10 minutes. The residue was dissolved in CH2Cl2 -(7.6 mL), and then the flask was charged with triethylamine (0.21 mL, 1.53 mmol) and 4-fluoro-3-(trifluoromethyl)benzenamine (0.916 mmol, 0.118 mL). The reaction mixture was allowed to stir at room temperature for 4 hrs. Upon completion, the reaction mixture was concentrated in vacuo. The residue was purified by automated chromatography (100% CH2Cl2) to yield N-(4-fluoro-3-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide. MS m/z=421 [M-2H]-, 422 [M-H]-. Calc’d for C15H10F4INO3: 423

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-4-methylbenzoic acid, its application will become more common.

Reference:
Patent; Amgen Inc.; US2007/54916; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com