Dichloromethane → 2-Bromo-6-cyclobutylpyridine

HRID 706566Notes

Reaction equation

HRID 706566 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.ClCCl.[Br-].[CH:13]1([Zn+])[CH2:16][CH2:15][CH2:14]1>[Cu](I)I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:13]2[CH2:16][CH2:15][CH2:14]2)[N:3]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 122742,6-DibromopyridineHCID 178419766HCID 178419766, compound

Product 1

HCID 457880262-Bromo-6-cyclobutylpyridineYield 55%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with dry THF (50 mL), 2,6-dibromopyridine (3.00 g, 12.7 mmol), copper iodide (0.555 g, 2.91 mmol) and PdCl2(dppf):dichloromethane adduct (1.09 g, 1.33 mmol). The mixture was purged with argon for 10 minutes, and then cyclobutyl zinc bromide (0.5 M in THF, 30.4 mL, 15.2 mmol) was added and the mixture stirred at ambient temperature for 2 hours. The mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (5% ethyl acetate/hexane) afforded 1.48 g (55%) of the title compound as an orange oil.

Workup

  1. customThe mixture was purged with argon for 10 minutes
  2. customThe mixture was quenched with saturated ammonium chloride solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d590e15c9cf74dc1b243ec44b72edbeb
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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