Pyridine → N-(5-bromopyridin-3-yl)acetamide

HRID 712699Notes

Reaction equation

HRID 712699 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:15](=[O:17])[CH3:16])[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 18624575N-(5-bromopyridin-3-yl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-5-bromopyridine (1.0 g, 5.78 mmol) and pyridine (1.3 mL, 12.9 mmol) in DCM (5 mL) is added acetic anhydride (0.6 mL, 6.358 mmol) dropwise. The mixture is stirred at room temperature for 17 h. The mixture is concentrated and the resulting crude product is purified by normal phase using 0-75% EtOAc in heptane as the gradient to afford N-(5-bromo-pyridin-3-yl)-acetamide (1.18 g, 95% yield).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe resulting crude product is purified by normal phase

Sources & evidence

ORD record
ord-5fae8ac9b23647509ab9238568673e54
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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