Cesium carbonate → racemic 4-(5-{1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine

HRID 732140Notes

Reaction equation

HRID 732140 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([C@H:13]([OH:15])[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:16][N:17]1[C:21](S(C)(=O)=O)=[N:20][N:19]=[C:18]1[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]([O:15][C:21]3[N:17]([CH3:16])[C:18]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)=[N:19][N:20]=3)[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 221514774-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineHCID 57838008(+)-(1R)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethanol

Product 1

HCID 24786188racemic 4-(5-{1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridineYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.57 g (2.54 mmol) (+)-(1R)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethanol, 0.64 g (2.68 mmol) 4-[4-methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyridine and 0.90 g (2.76 mmol) cesium carbonate were stirred at 65° C. for 6 h, followed by dilution with water. Extraction with EA, washing with aq. citric acid, drying over Na2SO4, followed by purification via chromatotron 2 mm (Hep/EA/MeOH=10/10/1) gave 0.81 g (83%) racemic 4-(5-{1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine. Prep. chiral separation on Chiralpak AD using 100% 2-propanol yielded 0.25 g of the title compound as the second eluting enantiomer. 1H NMR: 8.76 (d, 2 H), 8.07 (t, 1 H), 7.92-7.99 (m, 1 H), 7.60-7.68 (m, 2 H), 7.45-7.51 (m, 1 H), 7.41 (t, 1 H), 6.45 (q, 1 H), 3.66 (s, 3 H), 1.99 (d, 3 H)

Workup

  1. extractionExtraction with EA
  2. washwashing with aq. citric acid
  3. dry with materialdrying over Na2SO4
  4. customfollowed by purification via chromatotron 2 mm (Hep/EA/MeOH=10/10/1)

Sources & evidence

ORD record
ord-d9676a765d264f6eb41937ce148d67ff
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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