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p-Bromochlorobenzene → N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336407
Notes
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Reaction equation

HRID 336407 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]4[N:20]=[C:21]([NH2:23])[N:22]=[C:18]4[CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:23][C:21]2[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([CH2:7][N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[CH:9][CH:10]=4)[N:19]3[N:20]=2)=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 591864835-(4-(Morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59186222N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine
Yield 44.7%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.50 g, 1.6 mmol), 1-bromo-4-chlorobenzene (340 mg, 1.8 mmol), tris(dibenzylideneacetone)dipalladium (0) (147 mg, 0.16 mmol), cesium carbonate (782 mg, 2.4 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (94 mg, 0.16 mmol) in 1,4-dioxane (50 mL) was heated to reflux for 2 days. The reaction mixture was diluted with ethyl acetate (300 mL), and the resulting suspension was filtered though celite. Concentration of the filtrate in vacuo provided crude product, which was purified by flash column chromatography (petroleum ether→ethyl acetate) to give product (300 mg, 44% yield). LCMS (ESI) m/z: 421.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. filtrationthe resulting suspension was filtered though celite
  4. customConcentration of the filtrate in vacuo provided crude product, which
  5. customwas purified by flash column chromatography (petroleum ether→ethyl acetate)

Sources & evidence

ORD record
ord-adc6cebc29b64eae9f7868b2ce961408
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes