Sodium Acetate → HCID 68835322, compound

HRID 2112949Notes

Reaction equation

HRID 2112949 reaction equation
[NH2:1][C:2]1[N:20]=[C:5]2[CH:6]=[C:7](Br)[CH:8]=[C:9]([C:10]3[O:14][C:13]([CH2:15][C:16](=[O:18])[CH3:17])=[N:12][N:11]=3)[N:4]2[N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.CC([O-])=O.[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.CCO.O>[NH2:1][C:2]1[N:20]=[C:5]2[CH:6]=[C:7]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[CH:8]=[C:9]([C:10]3[O:14][C:13]([CH2:15][C:16](=[O:18])[CH3:17])=[N:12][N:11]=3)[N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 27343783-Pyridinylboronic acidHCID 68835927HCID 68835927, compound2×

Product 1

HCID 68835322HCID 68835322, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
105 °C

Procedure

1-[5-(2-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-[1,3,4]oxadiazol-2-yl]-propan-2-one (product of Step 2), (0.37 g, 1.1 mmol), 3-pyridyl boronic acid (0.2 g, 1.65 mmol) and NaOAc, (0.5 g, 5 mmol) were placed in a flask with 100 mL of 8:1:1 toluene/EtOH/water and placed under a N2 atmosphere. PdCl2(dppf), (0.09 g, 0.11 mmol) was added and the mixture was heated to 105° C. for two hours. The mixture was concentrated to dryness under reduced pressure and the residue taken up in 100 mL of 9:1 CH2Cl2/methanol. The mixture was filtered through celite and insoluble residue discarded. The filtrate was extracted with 1 N HCl (3×25 mL), and any residue in the aqueous removed by filtration. The aqueous filtrate was adjusted to pH 8 with K2CO3, resulting in a precipitate that was dried under vacuum to give 1-[5-(2-Amino-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-[1,3,4]oxadiazol-2-yl]-propan-2-one. MS (APCI+): m/z 336.1.

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. filtrationThe mixture was filtered through celite and insoluble residue
  3. extractionThe filtrate was extracted with 1 N HCl (3×25 mL)
  4. customany residue in the aqueous removed by filtration
  5. customresulting in a precipitate that
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-f5d5c1449320465e86ed0470d4173f6a
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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