Pyridine → (6-Bromo-pyridin-3-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

HRID 76063

Reaction equation

HRID 76063 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.B(O)(O)[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[N:15][CH:14]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Br:19][C:16]1[N:15]=[CH:14][C:13]([NH:1][C:2]2[CH:3]=[N:4][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:7]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 27627062-Bromopyridine-5-boronic acid

Product 1

HCID 87075507(6-Bromo-pyridin-3-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-6-trifluoromethyl pyridine (0.25 g, 1.2 mmol, 2.0 equiv) and 2-bromopyridyl-5-boronic acid (0.10 g, 0.62 mmol, 1.0 equiv) in 5 Ml dichloromethane was added pyridine (0.10 Ml, 1.2 mmol, 2.0 equiv), copper (II) acetate (0.17 g, 0.93 mmol, 1.5 equiv) and 4 Å molecular sieves. The heterogeneous reaction mixture was allowed to stir vigorously open to air overnight. The reaction was then filtered through Celite, concentrated in vacuo, and purified by silica gel chromatography to afford the title compound: (M+H)+319.9.

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-68dde0f62c6d49a88b922f8b3b6d019e
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Linked notes

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