4-(4-Bromophenyl)morpholine → Benzenamine, 4-(4-morpholinyl)-

HRID 472293Notes

Reaction equation

HRID 472293 reaction equation
CS(C1C=CC(C2C=CC3[N:15](N=C(N)N=3)C=2)=CC=1)(=O)=O.Br[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[N:28]1([C:25]2[CH:26]=[CH:27][C:22]([NH2:15])=[CH:23][CH:24]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 116228514-(4-Bromophenyl)morpholineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674814896-(4-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 75655Benzenamine, 4-(4-morpholinyl)-

Procedure

6-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-yl-phenyl)-amine was prepared from 6-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (50.0 mg, 0.173 mmol) and 4-(4-bromo-phenyl)-morpholine (51.0 mg, 0.211 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (20.0 mg, 0.0366 mmol) as the ligand in a manner analogous to Step 2d. The title compound was isolated as a yellow solid (0.011 g, 14%). MP=>300° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.41 (s, 1H), 9.28 (s, 1H), 8.09 (d, J=7.7 Hz, 2H), 8.03-7.96 (m, 3H), 7.64 (d, J=8.8 Hz, 1H), 7.59 (d, J=7.9 Hz, 2H), 6.93 (d, J=8.0 Hz, 2H), 3.77-3.71 (m, 4H), 3.28 (s, 3H), 3.05-3.00 (m, 4H). MS=450 (MH)+.

Sources & evidence

ORD record
ord-bcd12c64c20e4d7e910faf5b6afb4847
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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