1-Bromo-4-(methylsulphonyl)benzene → HCID 59612357, compound
Reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:11][C:9]2[N:10]=[C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]3[N:8]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]Participants
Procedure
N-(3-methyl-2-pyridinyl)-N′-carboethoxy-thiourea was prepared from 3-methyl-pyridin-2-ylamine (3.93 g, 0.0363 mol) in a manner analogous to Example 2a. Product was isolated as a yellow solid. 265b) 8-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from N-(3-methyl-2-pyridinyl)-N′-carboethoxy-thiourea (8.6 g, 36 mmol) in a manner analogous to Example 2b. Product was isolated as an off-white solid (3.96 g, 74%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.36 (d, J=6.6 Hz, 1H), 7.21 (d, J=6.8 Hz, 1H), 6.78 (dd, J=6.8 Hz, 6.8 Hz, 1H), 5.96 (bs, 2H), 2.39 (s, 3H). MS=149.0 (MH)+. 265c) (4-Methanesulfonyl-phenyl)-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine was prepared from 8-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (500 mg, 3.37 mmol) and 1-bromo-4-methanesulfonyl-benzene (973 mg, 1.23 mmol) in a manner analogous to Example 2d. Product was isolated as an off-white solid (0.369 g, 36%). MP=227-230° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.35 (s, 1H), 8.67 (d, J=6.9 Hz, 1H), 7.88 (d, J=8.9 Hz, 2H), 7.82 (d, J=8.9 Hz, 2H), 7.42 (d, J=7.1 Hz, 1H0, 6.99 (dd, J=7.1 Hz, 7.1 Hz, 1H), 3.14 (s, 3H). MS=303 (MH)+.
Sources & evidence
- ORD record
- ord-6a5562022d274cb1a3f404535c0a8091
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501936B2
Reaction notes
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