Pyridine → HCID 86634691, compound

HRID 76061Notes

Reaction equation

HRID 76061 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.B(O)(O)[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[N:11][CH:10]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Br:15][C:12]1[N:11]=[CH:10][C:9]([NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 1372541-Methyl-3-aminopyrazoleHCID 27627062-Bromopyridine-5-boronic acid

Product 1

HCID 86634691HCID 86634691, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-1H-pyrazol-3-ylamine (0.23 g, 2.3 mmol, 1.0 equiv) and 2-bromopyridyl-5-boronic acid (0.70 g, 3.5 mmol, 1.5 equiv) in 10 Ml dichloromethane was added pyridine (0.43 Ml, 5.4 mmol, 2.4 equiv), copper (II) acetate (0.63 g, 3.5 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: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.80 (s, 3H) 5.84 (s, 1H) 7.45 (d, J=8.59 Hz, 1H) 7.60 (d, J=2.02 Hz, 1H) 7.86 (dd, J=8.59, 3.03 Hz, 1H) 8.41 (d, J=2.78 Hz, 1H) 8.92 (s, 1H); (M+H)+255.1.

Workup

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

Sources & evidence

ORD record
ord-8ca3edaf574e4e59b8c46bbb28a0cfc7
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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