Pyrrolidine → 2-Bromo-4-(pyrrolidin-1-yl)pyridine

HRID 537261Notes

Reaction equation

HRID 537261 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[Br:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:7]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 8171042,4-Dibromopyridine

Product 2

HCID 105372692-Bromo-4-(pyrrolidin-1-yl)pyridineHCID 457879184-Bromo-2-pyrrolidin-1-ylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2,4-Dibromopyridine (1.0 g, 4.22 mmol) was dissolved in ethanol (40 mL) and pyrrolidine (1.733 ml, 21.11 mmol) was added. The reaction mixture was stirred at 70° C. for 20 hours. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo to give a pale yellow solid. The crude product was purified by chromatography on silica gel (gradient: 0-80% ethyl acetate in isohexane) to afford 2-bromo-4-(pyrrolidin-1-yl)pyridine (460 mg) as a white solid, and 4-bromo-2-(pyrrolidin-1-yl)pyridine (260 mg) as a white solid. LCMS (Method F, ES-API): RT 0.79 min, m+H=227.1/229.1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. customto give a pale yellow solid
  4. customThe crude product was purified by chromatography on silica gel (gradient: 0-80% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-a364ffb255a549ce8117bb7ccf0d9b56
Source dataset
uspto-grants-2014_10
Patent number
US08859774B2

Reaction notes

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