Pyridine → HCID 68704513, compound

HRID 1624909Notes

Reaction equation

HRID 1624909 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19].N1C=CC=CC=1.[N+]1([O-])C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:4]2[C:3](=[O:17])[C:2]([Br:1])=[N:7][N:6]([C:24]3[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=3)[C:18]#[N:19])[C:5]2=[O:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 12753Pyridine N-OxideHCID 27343253-Cyanophenylboronic acidHCID 687033544-(4-chlorobenzyl)-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 68704513HCID 68704513, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

According to Scheme 2 Step 3: To a solution of 6-bromo-4-(4-chlorobenzyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.600 g, 1.9 mmol) in DCM (8 ml) were added 3-cyanophenylboronic acid (0.42 g, 2.8 mmol), copper(II) acetate (0.069 g, 0.38 mmol), pyridine (0.3 g, 3.8 mmol) and pyridine N-oxide (0.2 g, 2.1 mmol) and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with a saturated sodium bicarbonate solution and extracted with ethyl acetate (×3). The combined organic layers were washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 30 g prepacked column, cyclohexane/ethyl acetate 85/15 to afford 3-(4-(4-chlorobenzyl)-6-bromo-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)benzonitrile (300 mg, 38%) which was used in the next step without any purification

Workup

  1. customThe reaction mixture was quenched with a saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were washed with water
  4. dry with materialwith brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography, 30 g

Sources & evidence

ORD record
ord-24e4d8b3f2af446394a0afb765a65c08
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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