Potassium Acetate → 3-Methyl-[1,2,3]triazolo[1,5-a]pyridin-5-ylboronic acid

HRID 879577Notes

Reaction equation

HRID 879577 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[N:9][C:10]([CH3:11])=[C:4]2[CH:3]=1.[B:12]1(B2OC(C)(C)C(C)(C)O2)[O:16]C(C)(C)C(C)(C)[O:13]1.CC([O-])=O.[K+]>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].C(Cl)Cl.O1CCOCC1>[CH3:11][C:10]1[N:9]=[N:8][N:5]2[CH:6]=[CH:7][C:2]([B:12]([OH:16])[OH:13])=[CH:3][C:4]=12

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 826605365-Bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine

Product 1

HCID 867003963-Methyl-[1,2,3]triazolo[1,5-a]pyridin-5-ylboronic acid

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a vial flushed with argon was added 5-bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine (424 mg, 2 mmol), PdCl2(dppf)-DCM (327 mg, 0.4 mmol), bis(pinacolato)diboron (660 mg, 2.6 mmol), and KOAc (589 mg, 6 mmol). Anhydrous dioxane (10 mL) was added, and the mixture was heated to 100° C. for 3 hours. After cooling to room temperature, the mixture was filtered over a plug of Celite, and concentrated to provide the crude product, which was used directly without further purification. LCMS-ESI+: calc'd for C7H9BN3O2: 178.1 (M+H+); Found: 178.04 (M+H+).

Workup

  1. customTo a vial flushed with argon
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered over a plug of Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4473cd2a509347d4862219db5590f92e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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