2-Bromoanisole → [5-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methoxyphenyl)-amine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29]>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]Participants
Procedure
[5-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-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-2-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]-(2-methoxyphenyl)-amine (52 mg, 38%) as a yellow powder following purification on a 12 g Isco silica gel column using 0-5% methanol in dichloromethane as an eluent. MP=88° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.78 (br s, 1H), 8.79 (m. 1H), 8.36 (d, J=7.1 Hz, 1H), 8.20 (d, J=7.1 Hz, 1H), 8.12 (d, J=7.1 Hz, 1H), 8.00 (s, 1H), 7.89 (t, J=12.9, 8.2, 1H), 7.72 (m, 1H), 7.65 (d, J=9.4 Hz, 1H), 7.38 (d, J=8.2 Hz, 1H), 7.05 (d, J=5.9 Hz, 1H), 6.92 (m, 2H), 3.87 (s, 3H), 3.32 (s, 3H). MS=395 (MH)+.
Sources & evidence
- ORD record
- ord-59d196d445614fcdbb3d1f0e98d38e7e
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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