Potassium Acetate → 3-Methoxypyridine-4-boronic acid

HRID 1431579Notes

Reaction equation

HRID 1431579 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][CH3:10].[B:11]1(B2OC(C)(C)C(C)(C)O2)[O:15]C(C)(C)C(C)(C)[O:12]1.C([O-])(=O)C.[K+]>O1CCOCC1.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]>[CH3:10][O:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[B:11]([OH:15])[OH:12]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 457897214-Bromo-3-methoxypyridine hydrochloride

Product 1

HCID 467390193-Methoxypyridine-4-boronic acid

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromo-3-methoxypyridine hydrochloride (0.34 g, 1.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.13 g, 0.16 mmol), bis(pinacolato)diboron (0.47 g, 1.85 mmol), and potassium acetate (0.75 g, 7.7 mmol) in dry 1,4-dioxane (6.0 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 19 h, the reaction was cooled to rt then filtered. After concentration, the residue was identified as 3-methoxypyridin-4-ylboronic acid that was used without purification.

Workup

  1. customwas degassed by nitrogen
  2. temperaturethe reaction was cooled to rt
  3. filtrationthen filtered
  4. concentrationAfter concentration
  5. customwas used without purification

Sources & evidence

ORD record
ord-f4fad70041ba4349ae22d83393d2a241
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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