1-Bromo-4-(methylsulphonyl)benzene → HCID 57514092, compound

HRID 1889847Notes

Reaction equation

HRID 1889847 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:31][S:28]([C:25]1[CH:26]=[CH:27][C:22]([NH:20][C:18]2[N:19]=[C:12]3[C:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=4)=[CH:16][CH:15]=[CH:14][N:13]3[N:17]=2)=[CH:23][CH:24]=1)(=[O:30])=[O:29]

Participants

4

Reactant 3

HCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 575023768-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 57514092HCID 57514092, compound

Procedure

(4-Methanesulfonyl-phenyl)-[8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-bromo-4-methanesulfonyl-benzene (75.0 mg, 0.319 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (30.0 mg, 0.0549 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as tan solid (0.063 g, 55%). MP=280-282° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.56 (d, J=5.7 Hz, 1H), 8.22 (d, J=8.0 Hz, 2H), 8.10 (d, J=7.6 Hz, 2H), 7.92 (d, J=7.8 Hz, 2H), 7.77 (d, J=7.3 Hz, 2H), 7.72 (d, J=7.3 Hz, 1H), 7.32 (s, 1H), 7.14-7.09 (m, 1H), 3.11 (s, 3H), 3.06 (s, 3H). MS=443 (MH)+.

Sources & evidence

ORD record
ord-4ce0cbfc057242d4bb1ac866df1754f2
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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