Water → {3,5-dichloro-4-[6-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester

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Reaction Steps

To a solution of (3,5-dichloro-4-formylphenoxy)-acetic acid methyl ester (524 mg, 2.0 mmol) and 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (510 mg, 2.0 mmol) (Example 5-1, step 6) in DMSO (15 mL) was added Yb(OTf)3 (248 mg, 0.4 mmol) and the solution was stirred at ambient temperature overnight. The mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried with MgSO4, filtered and concentrated. Purification by HPLC (0-80% MeCN/water) gave {3,5-dichloro-4-[6-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester as a white solid. MS (m/z) 498.1 (M+1); 1H-NMR (Methanol-d4, 400 MHz): δ 8.36 (d, 1H), 8.09 (dd, 1H), 7.87 (dd, 1H), 7.49 (d, 1H), 7.46 (dd, 1H), 7.31 (s, 2H), 7.16 (d, 1H), 4.93 (s, 2H), 3.83 (s, 3H), 2.31 (s, 3H), 2.28 (s, 3H).

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