p-Toluenesulfonic acid → 3-Bromo-4-cyclopent-1-enyl-pyridine

HRID 572432Notes

Reaction equation

HRID 572432 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1(O)[CH2:23][CH2:22][CH2:21][CH2:20]1.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH2:23][CH2:22][CH2:21][CH:20]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 70982889HCID 70982889, compound

Product 1

HCID 709821203-Bromo-4-cyclopent-1-enyl-pyridineYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

PTSA (819 mg, 4.315 mmol) was added portionwise to a stirred mixture of 1-(3-bromo-pyridin-4-yl)-cyclopentanol (I-34a: 520 mg, 2.15 mmol) in 25 mL of toluene. The resulting mixture was heated to reflux at 120° C. for 4 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was concentrated, basified with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated to afford the crude product. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 350 mg of the product (73% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8062522ffd8e4708bc8890e0e18c6905
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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