Triethylamine → Ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

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Reaction Steps

To a stirred solution of 3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline (prepared in Example 1, Step B; 0.78 g, 3.0 mmol), triethylamine (0.84 mL, 6.0 mmol), and CH2Cl2 (5 mL) was added a solution of ethyl 2-chloro-2-oxoacetate (0.45 g, 3.3 mmol) in CH2Cl2 (1 mL) dropwise at room temperature. Stirring was continued for 15 minutes. The mixture was washed with water (3×5 mL), dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by Biotage Flash 40 silica gel chromatography, eluting with 30% EtOAc/hexanes, then 1:1 EtOAc/hexanes. The product was obtained as a white powder (656 mg, 61%). 1H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 8.53 (d, J=6 Hz, 1H), 7.85 (d, J=12 Hz, 1H), 7.76 (d, J=6 Hz, 1H), 7.58 (d, J=6 Hz, 1H), 7.39 (d, J=9 Hz, 1H), 7.30 (d, J=9 Hz, 1H), 6.52 (d, J=6 Hz, 1H), 4.44 (q, J=7 Hz, 2H), 1.44 (t, J=7 Hz, 3H). LRMS (APCI pos) m/e 361 (M+1). HPLC: 99% purity (220 nm).

Provenance & Evidence