Cesium carbonate → 2-[4-(3-methoxy-4-pyridin-2-ylphenyl)-2H-1,2,3-triazol-2-yl]pyridine

HRID 915906Notes

Reaction equation

HRID 915906 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[N:11][NH:12][CH:13]=2)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].[O-]S(C(F)(F)F)(=O)=O.F[N+:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:13]=[N:12][N:11]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 178487641HCID 178487641, compound

Product 1

HCID 99055252-[4-(3-methoxy-4-pyridin-2-ylphenyl)-2H-1,2,3-triazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[2-methoxy-4-(1H-1,2,3-triazol-4-yl)phenyl]pyridine (180 mg, 0.71 mmol) in anhydrous MeOH was added Cs2CO3 (462 mg, 1.42 mmol) and 1-fluoropyridinium triflate (350 mg, 1.42 mmol). The resulting reaction mixture was stirred overnight. The mixture was partitioned between 10% aqueous NaOH (10 ml) and EtOAc (60 mL). The phases were separated and the aqueous layer was extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified on silica gel (1:2 hexane-ethyl acetate) to afford 2-[4-(3-methoxy-4-pyridin-2-ylphenyl)-2H-1,2,3-triazol-2-yl]pyridine which was dissolved in ether and HCl (1N in ether) was added. The solution was filtered to give a HCl salt as white solid. 1H NMR (500 MHz, CD3OD) δ 8.86-8.47 (m, 1H), 8.72-8.68 (m, 1H), 8.64-8.62 (m, 2H), 8.39-8.37 (m, 1H), 8.26-8.25 (m, 1H), 8.15-8.11 (m, 1H), 8.07-8.04 (m, 1H), 8.02 (m, 1H), 7.91-7.80 (m, 2H), 7.60 (m, 1H). MS (ESI) 330 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. customThe mixture was partitioned between 10% aqueous NaOH (10 ml) and EtOAc (60 mL)
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×60 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel (1:2 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7b9707cfd6234eedb95e54e5d6cac697
Source dataset
uspto-grants-2007_09
Patent number
US07268151B2

Reaction notes

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