2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → [8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 472315Notes

Reaction equation

HRID 472315 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH2:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1.Br[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH:21]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 534153291-(3-Bromophenyl)-4-methylpiperazineHCID 575023708-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 67479000[8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine

Procedure

[8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.312 mmol) and 1-(3-bromo-phenyl)-4-methyl-piperazine (90.0 mg, 0.353 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (34.0 mg, 0.0622 mmol) as the ligand in a manner analogous to Step 2d and was isolated as a pale yellow foam (0.069 g, 53%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.40 (d, J=6.5 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.54 (d, J=7.3 Hz, 1H), 7.43-7.35 (m, 2H), 7.19 (d, J=7.9 Hz, 1H), 7.11-7.02 (m, 2H), 6.94-6.89 (m, 2H), 6.79 (s, 1H), 6.55 (d, J=7.9 Hz, 1H), 3.81 (s, 3H), 3.27-3.22 (m, 4H), 2.60-2.55 (m, 4H), 2.36 (s, 3H). MS=415 (MH)+.

Sources & evidence

ORD record
ord-26fc1e2fcccd4199b6ad5bbb1e94afa5
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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