The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.
Application of 108078-14-4,Some common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-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.
EXAMPLE 131; 122 Dioxanel-d-Iodo-S-methyl-benzoylaminoHndan-l-carboxylic Acid Ethyl EsterA 10OmL round bottom flask is charged with 2-Iodo-3-methylbenzoic Acid (1.92g, 7.3 lmmol) and dry DCM (25mL). A stirring bar is added and stirring initiated. After 5min, HTBU (2.37g, 7.3 lmmol) is added. After 5min, the 2-amino-indane-2-carboxylic Acid Ethyl Ester (1.5Og, 7.31mmoles) is added followed by DIPEA (3.2mL, 18.37mmol). The reaction is allowed to stir for 118 hours. Analysis by tic of the reaction mixture (silica, 15% iPrOH/Dischloromethane) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (70 mL). This is washed with dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 x 3OmL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of white solid. This material is dissolved in DCM (15mL). This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAC in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active elutant were collected. Fractions 10 through 15 are combined and evaporated in vacuo to constant weight to give 2-(2-iodo-3-methyl- benzoylamino)-indan-2-carboxylic acid ethyl ester 1.04g of white solid.EXAMPLE 175; 149 l-d-Iodo-S-methyl-benzoylaminoHndane-l-carboxylic acid ethyl ester (175):A 10OmL round bottom flask is charged with 2-iodo-3-methylbenzoic acid (1.92g, 7.31mmol) and dry DCM (25mL). A stirring bar is added and stirring is initiated. After 5min, the HBTU (2.37g, 7.31mmol) is added. After 5min, the 2-amino-indane-2-carboxylic acid ethyl ester(1.5g, 7.31mmol) is added followed by N,N-diisopropylethyl-amine (3.2mL, 18.37mmol). The reaction is allowed to stir for 118h. Analysis by tic of the reaction mixture (silica, 15% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (7OmL). This is washed dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 X 3OmL) and brine (3OmL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of a white solid. This material is dissolved in 15mL of DCM. This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAc in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active eluent are collected. Fractions 10 through 15 are combined and evaporated in vacuo. Pumping to constant weight gives 1.04g a white solid material.1H NMR (300 MHz, DMSO-d6): delta 1.20 (t, 3 H), 2.39 (s, 3 H), 3.52 (dd, 4H), 4.15 (q, 2H), 6.79 (d, IH), 6.97 (d, IH), 7.16 – 7.24 (m, 4H), 7.28 – 7.38 (m, 2H), 9.15 (s, IH). LC/MS m/z = 450.
The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com