Water → 4-(5-{2-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-vinyl}-4-ethyl-4H-[1,2,4]triazol-3-yl)pyridine

HRID 639825Notes

Reaction equation

HRID 639825 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]1[CH:14]=O)[CH3:2].Br.[Cl:17][C:18]1[CH:19]=[C:20]([N:24]2[N:28]=[N:27][C:26]([CH2:29]P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:25]2)[CH:21]=[CH:22][CH:23]=1.C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([N:24]2[N:28]=[N:27][C:26]([CH:29]=[CH:14][C:4]3[N:3]([CH2:1][CH3:2])[C:7]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)=[N:6][N:5]=3)=[N:25]2)[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 860676734-Ethyl-5-pyridin-4-yl-4H-[1,2,4]triazole-3-carbaldehydeHCID 178419577HCID 178419577, compound

Product 1

HCID 684327624-(5-{2-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-vinyl}-4-ethyl-4H-[1,2,4]triazol-3-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Ethyl-5-pyridin-4-yl-4H-[1,2,4]triazole-3-carbaldehyde (56.4 mg, 0.279 mmol) was dissolved in dimethylformamide (2 mL) and added to a vial containing 2-(3-chloro-phenyl)-5-[(triphenyl-λ5-phosphanyl)-methyl]-2H-tetrazole hydrobromide (165.1 mg, 0.307 mmol) dissolved in dimethylformamide (2 mL). After addition of DBU (84.9 mg, 0.558 mmol), the vial was capped and the reaction was allowed to stir at room temperature for two hours. It was then heated at 80° C. for 1.5 hours. After cooling, water was added and an aqueous workup was done extracting with ethyl acetate three times. The combined organic layers were washed with water twice, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by an SPE tube (5% MeOH/CH2Cl2) to yield the title compound as a white solid. 1H NMR (CDCl3) δ (ppm): 8.84 (d, 2H), 8.22 (m, 1H), 8.10 (d oft, 1H), 8.04 (d, 1H), 7.67 (d, 1H), 7.64 (m, 2H), 7.51 (m, 2H), 4.27 (q, 2H), 1.51 (t, 3H).

Workup

  1. additionadded to
  2. customthe vial was capped
  3. temperatureIt was then heated at 80° C. for 1.5 hours
  4. temperatureAfter cooling
  5. extractionan aqueous workup was done extracting with ethyl acetate three times
  6. washThe combined organic layers were washed with water twice
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by an SPE tube (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e3f877881fcb4e8cb3d405efcf73af5b
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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