The important role of 82998-57-0

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.

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