3-Bromoanisole → [5-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-methoxyphenyl)-amine

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Reaction Steps

[5-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-methoxyphenyl)-amine was prepared from 5-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100 mg, 0.35 mmol) and 1-bromo-3-methoxy benzene (52 μL, 0.42 mmol) in a manner analogous to Example 77 to yield [5-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-methoxyphenyl)-amine (104 mg, 75%) as a yellow powder following purification on a 12 g Isco silica gel column using 0-5% methanol in dichloromethane as an eluent. MP=180° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.66 (s, 1H), 8.62 (m, 1H), 8.40 (d, J=8.0 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.87 (t, J=16.1 Hz, 8.0 Hz, 1H), 7.68 (m, 2H), 7.32 (m, 2H), 7.25 (d, J=8.6 Hz, 1H), 7.15 (t, J=16.5 Hz, 8.0 Hz, 1H), 6.45 (dd, J=8.0 Hz, 2.7 Hz, 1H), 3.69 (s, 3H), 3.33 (s, 3H). MS=395 (MH)+.

Provenance & Evidence