Water → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101317Notes

Reaction equation

HRID 2101317 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2C=CN=C(NN)[C:21]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:16][CH:15]=1.O>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:11]=[CH:12][N:8]3[C:1](=[O:2])[NH:3][N:10]=[C:9]3[C:21]=2[C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 577994604-(4-Chlorophenyl)-2-hydrazinyl-3,4'-bipyridine

Product 1

HCID 577993927-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1,1′-carbonyldiimidazole (2.5 g, 15.4 mmol) in THF (15 mL) at room temperature under argon was added 4-(4-chlorophenyl)-2-hydrazinyl-3,4′-bipyridine (0.92 g, 3.1 mmol). The reaction mixture was stirred at room temperature for 45 min. The reaction mixture was then concentrated under vacuum to produce a yellow solid. This solid was stirred in an ice bath and water (25 mL) was added. Solid was collected by filtration and further washed with water (15 mL×2). After drying in an oven at 50° C. under reduced pressure overnight, 960 mg of the title compound was obtained as a yellow solid. HPLC/MS: retention time=1.985 min, [M+H]+=323. 1H NMR (DMSO-d6, 500 MHz): δ 12.61 (s, 1H), 8.50 (d, J=6.05 Hz, 2H), 7.94 (d, J=7.15 Hz, 1H), 7.36 (d, J=8.2 Hz, 2H), 7.23 (d, J=6.05 Hz, 2H), 7.18 (d, J=8.2 Hz, 2H), 6.68 (d, J=7.15 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. customto produce a yellow solid
  3. stirringThis solid was stirred in an ice bath
  4. filtrationSolid was collected by filtration
  5. washfurther washed with water (15 mL×2)
  6. customAfter drying in an oven at 50° C. under reduced pressure overnight

Sources & evidence

ORD record
ord-e63319b9eae244999cc3c33bb32e754e
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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