Ammonium Acetate → 2-Methylpyridine-4-boronic acid

HRID 2055084Notes

Reaction equation

HRID 2055084 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12]C(C)(C)C(C)(C)[O:9]2)[CH:5]=[CH:4][N:3]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+]>CC(C)=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([B:8]([OH:12])[OH:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 23667635Sodium periodate

Product 1

HCID 41926642-Methylpyridine-4-boronic acidYield 100%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (920 mg, 4.2 mmol) in acetone/water [70 mL (1:1)] was added sodium periodate (2.69 g, 12.6 mmol) and ammonium acetate (810 mg, 10.5 mmol), and allowed to stir at room temperature for 12 hours. The reaction mixture was filtered and concentrated under vacuum to afford desired 2-methyl-4-pyridineboronic acid (575 mg). (Note: This material can be used w/o further purification in Example 13.)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f0a4fb535404da4bf9204fae9a96a12
Source dataset
uspto-grants-2008_02
Patent number
US07332486B2

Reaction notes

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