Pyridine → HCID 67124891, compound

HRID 926839Notes

Reaction equation

HRID 926839 reaction equation
[N+:1]([C:4]1[N:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[N+:1]([C:4]1[N:8]=[CH:7][N:6]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:21])([F:20])[F:9])[CH:16]=2)[N:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 178526901HCID 178526901, compound

Product 1

HCID 67124891HCID 67124891, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

Into a 250-mL round bottom flask, was placed a solution of 3-nitro-1H-1,2,4-triazole (2 g, 17.54 mmol, 1.00 equiv) in dichloromethane (100 mL), 3-(trifluoromethyl)phenylboronic acid (6.66 g, 35.05 mmol, 2.00 equiv), Cu(OAc)2 (4.79 g, 26.32 mmol, 1.50 equiv), pyridine (2.77 g, 35.06 mmol, 2.00 equiv), and molecular sieves (5.2 g). The resulting solution was stirred overnight at 30° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20-1:10) to give 2.2 g (49%) of product as a white solid.

Workup

  1. customInto a 250-mL round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. washeluted with ethyl acetate/petroleum ether (1:20-1:10)

Sources & evidence

ORD record
ord-fbe51e9d7b324e1ca31a5aa6fc5883f1
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

Loading…