2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → [3-(4-Methyl-piperazin-1-yl)-phenyl]-[8-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH2:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Br[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([C:24]2[CH:25]=[C:26]([NH:18][C:16]3[N:17]=[C:10]4[C:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:4][CH:5]=5)=[CH:14][CH:13]=[CH:12][N:11]4[N:15]=3)[CH:27]=[CH:22][CH:23]=2)[CH2:29][CH2:30]1Participants
Reactant 3
Product 1
Procedure
[3-(4-Methyl-piperazin-1-yl)-phenyl]-[8-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine was prepared from 8-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.270 mmol) and 1-(3-bromo-phenyl)-4-methyl-piperazine (80.0 mg, 0.314 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (30.0 mg, 0.0549 mmol) as the ligand in a manner analogous to Step 2d and was isolated as a yellow solid (0.043 g, 35%). MP=234-236° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.46 (d, J=7.0 Hz, 1H), 8.15 (d, J=7.7 Hz, 2H), 7.76 (d, J=8.2 Hz, 2H), 7.62 (d, J=7.2 Hz, 1H), 7.48 (s, 1H), 7.25-7.19 (m, 1H), 7.02-6.97 (m, 1H), 6.92 (d, J=7.3 Hz, 1H), 6.83 (s, 1H), 6.59 (d, J=7.8 Hz, 1H), 3.30-3.25 (m, 4H), 2.62-2.57 (m, 4H), 2.37 (s, 3H). MS=435 (MH)+.
Sources & evidence
- ORD record
- ord-71d02cf7b3b2469293c8cd488973d073
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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