3-Aminopyridine → N-(2-chloro-5-(trifluoromethyl)pyridin-4-yl)pyridin-3-amine

HRID 1887676Notes

Reaction equation

HRID 1887676 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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:1][C:2]1[CH:7]=[C:6]([NH:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27737912-Chloro-4-iodo-5-(trifluoromethyl)pyridine

Product 1

HCID 58155011N-(2-chloro-5-(trifluoromethyl)pyridin-4-yl)pyridin-3-amine

Reagents, catalysts & solvents 2

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

Procedure

Method B was applied to a mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (105 mg, 0.34 mmol), 3-aminopyridine (34 mg, 0.36 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), xantphos (20 mg, 0.035 mmol) and cesium carbonate (225 mg, 0.69 mmol) in dioxane (4.5 ml).

Sources & evidence

ORD record
ord-410a0c8af54f4de19f7f3f9b405a0d4e
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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