Dichloromethane → HCID 69628775, compound

Participants

Reaction Steps

To a solution of K2CO3 (11.39 g, 82.41 mmol) in 41 mL H2O was added 280 mL dioxane, a 2:1 mixture of 3-bromo-4-methoxymethoxy-5-iodobenzoic acid ethyl ester and 3,5-dibromo.4-methoxymethoxybenzoic acid ethyl ester (4.85 g, 13.74 mmol) and 3-methylphenyl boronic acid (4.1 g, 27.47 mmol) at room temperature. The reaction was degassed and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with CH2Cl2 (224 mg, 0.248 mmol) was added. The reaction was stirred for 2d then more of the catalyst was added (56 mg, 0.0687 mmol). The reaction was stirred for one more day and the reaction was worked up as in Step 1 of Example 135 to give crude material that was subjected to flash column chromatography (5% EtOAc:95% Hexanes). The major product from the column was further purified by prep HPLC to give 1.44 g, 23% of a white solid. 1H NMR (CDCl3) a 1.33 (t, J=8.18 Hz, 3H); 2.37 (s, 12H); 2.69 (s, 3H), 4.33-4.40 (m, 4H); 6.97 (s, 2H); 7.20 (m, 4H); 7.97 (s, 2H).

Provenance & Evidence