5-Chloro-2-phenylpyridine → 5-Ethyl-2-phenylpyridine

HRID 713558Notes

Reaction equation

HRID 713558 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:14]([Mg]Br)[CH3:15]>C1COCC1>[CH2:14]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1)[CH3:15]

Participants

4

Reactant 2

HCID 27628665-Chloro-2-phenylpyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 5978535-Ethyl-2-phenylpyridineYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-2-phenylpyridine (16 g, 84 mmol) and Ni(dppe)Cl2 (0.891 g, 1.687 mmol) were added to 300 mL of THF and the reaction mixture was degassed with nitrogen for 20 min. before being cooled to 0° C. Ethylmagnesium bromide (169 mL, 169 mmol) was added dropwise over a period of 60 min. and the reaction mixture stirred for and additional 3 h at before warming to room temperature overnight. The reaction mixture was recooled to 0° C. and quenched with 250 mL of water, extracted with EtOAc and the organic layer dried over sodium sulfate and filtered. The crude material was chromatographed on silica with 95/5 hexane/EtOAc to give 2.9 g (19%) of 5-ethyl-2-phenylpyridine as a white solid.

Workup

  1. customthe reaction mixture was degassed with nitrogen for 20 min.
  2. temperaturebefore warming to room temperature overnight
  3. customwas recooled to 0° C.
  4. customquenched with 250 mL of water
  5. extractionextracted with EtOAc
  6. dry with materialthe organic layer dried over sodium sulfate
  7. filtrationfiltered
  8. customThe crude material was chromatographed on silica with 95/5 hexane/EtOAc

Sources & evidence

ORD record
ord-501eb203d6c542168dea71438a871f8d
Source dataset
uspto-grants-2015_11
Patent number
US09184397B2

Reaction notes

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