Cesium carbonate → HCID 86650769, compound

HRID 875242Notes

Reaction equation

HRID 875242 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[CH:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[N:24]=1>CC#N>[Br:22][C:23]1[N:24]=[C:25]([CH2:29][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 136331258HCID 136331258, compound

Product 1

HCID 86650769HCID 86650769, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-hydroxy-1-(4-methyl-4H-1,2,4-triazol-3-yl)-1-phenylmethanimine (0.45 g, 2.22 mmol, 1.0 eq.) in 20 ml of MeCN was added Cs2CO3 (0.795 g, 2.44 mmol, 1.1 eq.) followed by Kl (0.0365 g, 0.22 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-6-(bromomethyl)pyridine (0.586 g, 2.33 mmol, 1.05 eq.) in one portion. The reaction was stirred for 4 h at room temperature. The solid was removed by filtration and washed with 250 ml of fresh MeCN. The filtrate was evaporated, and 500 ml of EtOAc were added. The organic layer was washed with H2O and dried over MgSO4 then concentrated. Chromatography of the crude on silica gel gave N-[(6-bromopyridin-2-yl)methoxy]-1-(4-methyl-4H-1,2,4-triazol-3-yl)-1-phenylmethanimine (0.748 g, 90% yield) as a yellow oil.

Workup

  1. customThe solid was removed by filtration
  2. washwashed with 250 ml of fresh MeCN
  3. customThe filtrate was evaporated
  4. addition500 ml of EtOAc were added
  5. washThe organic layer was washed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-0f1e69ad048749cdba47e0f4ccafb964
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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