Pyridine → 1-[2-(5-Bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanone

HRID 712754

Reaction equation

HRID 712754 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:7]=1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:19](=[O:21])[CH3:20])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 44038153-Bromo-5-(pyrrolidin-2-yl)pyridine

Product 1

HCID 1176672401-[2-(5-Bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanoneYield 132%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-(2-pyrrolidinyl)pyridine (200 mg, 0.881 mmol) and pyridine (0.2 mL, 1.96 mmol) in DCM (1 mL) in a 8-mL vial is added acetic anhydride (0.093 mL, 0.969 mmol) dropwise. The mixture is stirred at room temperature for 2.5 h. The mixture is concentrated. The resulting crude product is purified by normal phase chromatography using 0-4.5% MeOH in DCM as the gradient to afford 1-[2-(5-bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanone (313 mg, 83% yield).

Workup

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

Sources & evidence

ORD record
ord-621fe542518d4dd4a7d446037a497fb3
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Linked notes

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