4-(Methanesulfonyl)phenylboronic acid → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methoxy-phenyl)-amine
Reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22]>>[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][CH3:19])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=1)(=[O:23])=[O:22]Participants
3
Procedure
[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2-methoxy-phenyl)-amine was prepared from (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine (100.0 mg, 0.3133 mmol) and (4-methylsulfonylphenyl)boronic acid (75.0 mg, 0.375 mmol) in a manner analogous to Step 2c and was isolated as a pale yellow solid (0.097 g, 78%). MP=211-213° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.53-8.49 (m, 1H), 8.38 (dd, J=8.0, 1.3 Hz, 1H), 8.24 (d, J=8.4 Hz, 2H), 8.10 (d, J=8.5 Hz, 2H), 7.66-7.62 (m, 1H), 7.61 (s, 1H), 7.08-6.89 (m, 4H), 3.92 (s, 3H), 3.11 (s, 3H). MS=395 (MH)+.
Sources & evidence
- ORD record
- ord-6f81dd18efac4d73bc700c6ec4e4ef6b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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