Pyridine → 3-Bromo-5-(1-methanesulfonyl-pyrrolidin-2-yl)-pyridine

HRID 712753

Reaction equation

HRID 712753 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.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:20]([CH3:19])(=[O:22])=[O:21])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 44038153-Bromo-5-(pyrrolidin-2-yl)pyridine

Product 1

HCID 1176674783-Bromo-5-(1-methanesulfonyl-pyrrolidin-2-yl)-pyridineYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-bromo-5-(2-pyrrolidinyl)pyridine (0.2 g, 0.881 mmol) and pyridine (0.157 mL, 1.937 mmol) in DCM (1 mL) is added methanesulfonyl chloride in DCM (1 mL) dropwise. The mixture is stirred at room temperature for 2 h. The mixture is concentrated. The resulting crude product is purified by normal phase chromatography using 0-3% MeOH in DCM as the gradient to afford 3-bromo-5-(1-methanesulfonyl-pyrrolidin-2-yl)-pyridine (211.2 mg, 79% yield).

Workup

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

Sources & evidence

ORD record
ord-b06947c158c34beab6694062b2731c89
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Linked notes

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