Acetic Anhydride → 2-Acetamidopyridine-5-boronic acid pinacol ester

HRID 925502Notes

Reaction equation

HRID 925502 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[CH3:15][C:16]1([CH3:30])[C:20]([CH3:22])([CH3:21])[O:19][B:18]([C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=2)[O:17]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:22][C:20]1([CH3:21])[C:16]([CH3:30])([CH3:15])[O:17][B:18]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:8](=[O:10])[CH3:9])=[N:27][CH:28]=2)[O:19]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 177502022-Acetamidopyridine-5-boronic acid pinacol esterYield 63.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-dimethylaminopyridine (17 mg, 0.139 mmol), triethylamine (0.19 mL, 1.36 mmol) and acetic anhydride (153 mg, 1.50 mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg, 1.36 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30 mL of dichloromethane, washed with 50 mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225 mg of the product.

Workup

  1. washwashed with 50 mL of a saturated aqueous solution of ammonium chloride
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4117e6a463004cd196e5b93283521b45
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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