1,2-Dimethoxyethane → 2-Chloro-4-(4-cyclopentylphenyl)pyridine

HRID 1844925Notes

Reaction equation

HRID 1844925 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH:9]1([C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:17]2[CH:16]=[CH:15][C:14]([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 15165112-Chloro-4-iodopyridineHCID 41979984-Cyclopentylbenzeneboronic acid

Product 1

HCID 901215232-Chloro-4-(4-cyclopentylphenyl)pyridineYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-iodopyridine (6.43 g, 26.3 mmol), (4-cyclopentylphenyl)boronic acid (5.0 g, 26.3 mmol), Pd(Ph3P)4 (0.0.91 g 0.79 mmol), sodium carbonate (8.37 g, 79 mmol), DME (257 mL) and water (64 mL) was degassed with nitrogen and then refluxed overnight. The reaction mixture was concentrated and extracted with ethyl acetate. The the ethyl acetate layer was dried on Na2SO4 and then further purified by column chromatography using dichloromethane in hexanes and then vacuum distilled to give 2-Chloro-4-(4-cyclopentylphenyl)pyridine (4.6 g, 68% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe the ethyl acetate layer was dried on Na2SO4
  6. customfurther purified by column chromatography
  7. distillationvacuum distilled

Sources & evidence

ORD record
ord-0671f15164b74353b535019591e8b25e
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

Loading…