Tributyl(5-fluorobenzofuran-2-yl)stannane → 2-{2-[5-(5-Fluorobenzofuran-2-yl)pyridin-3-yl]-6-propylpyrimidin-4-ylamino}-4-methylpentanoic acid (3-ethoxypropyl) amide

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Reaction Steps

Under an atmosphere of argon, a solution of tributyl(5-fluorobenzofuran-2-yl)stannane (17 mg), 2-[2-(5-bromopyridin-3-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl)amide (20 mg) and (PPh3)2PdCl2 (2 mg) in N,N-dimethylformamide (1 mL) was heated at 80° C. for 12 h and then quenched with water (10 mL). The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic extracts were dried over sodium sulfate and concentrated. The crude product was purified by semi-preparative HPLC to give 4.6 mg of 2-{2-[5-(5-fluorobenzofuran-2-yl)pyridin-3-yl]-6-propylpyrimidin-4-ylamino}-4-methylpentanoic acid (3-ethoxypropyl) amide as a TFA salt. ESI-MS (m/z) 562 [M+H]+.

Provenance & Evidence