3,4,5-Trimethoxyaniline → 5-({6-[(3,4,5-trimethoxyphenyl)amino]pyrazin-2-yl}oxy)-2,3-dihydro-1H-inden-1-one

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Reaction Steps

Using Method EE with 2-chloro-6-(indanone-5-oxy)-pyrazine (200 mg, 0.77 mmol) and 3,4,5-trimethoxyaniline (169 mg, 0.92 mmol), and purification by column chromatography (AcOEt), the title compound was obtained (61 mg). Yield: 20%. 1H NMR (250 MHz, DMSO-d6) δ 2.68 (t, 2H, H3, J=5.6 Hz), 3.08 (t, 2H, H2, J=5.0 Hz), 3.39 (s, 6H, [CH3O]3+5), 3.55 (s, 3H, [CH3O]4), 6.77 (s, 2H, Harom2′+6′), 7.21 (dd, 1H, Harom 6, Jm=1.9 Hz, Jo=8.3 Hz), 7.40 (s, 1H, Harom 4), 7.68 (d, 1H, Harom 7, J=8.3 Hz), 7.84 (s, 1H, HPz 5), 8.02 (s, 1H, HPz 3), 9.62 (s, 1H, NH). m/z: 408.1 [(M+H)+, calcd for C22H21N3O5 407.1].

Provenance & Evidence