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

HRID 390937

Reaction equation

HRID 390937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:4][N:3]=1.C(N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(Cl)Cl>[CH3:15][C:10]1([CH3:16])[C:11]([CH3:14])([CH3:13])[O:12][B:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:24](=[O:26])[CH3:25])=[N:3][CH:4]=2)[O:9]1

Participants

5

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 ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (120 mg) in dry DCM (3 ml) and triethylamine (1.5 equiv., 114 uL) was added acetic anhydride (1.1 equiv., 57ul) and the reaction mixture was stirred at room temperature overnight. Dichloromethane/brine extraction and purification on silica gave 66 mg of N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl]-acetamide.

Workup

  1. extractionDichloromethane/brine extraction and purification on silica

Sources & evidence

ORD record
ord-2941b3bf7cfa4cc6a87b286261c30b3a
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Linked notes

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