Cesium carbonate → 3-(Cyclohex-1-en-1-yl)pyridine

HRID 337776Notes

Reaction equation

HRID 337776 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1(B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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>[C:8]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 133194903-(Cyclohex-1-en-1-yl)pyridineYield 99%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromopyridine (0.38 g, 2.40 mmol), 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.50 g, 2.40 mmol), tetrakis(triphenylphosphine)palladium (0) (0.14 g, 0.12 mmol) and cesium carbonate (1.72 g, 5.29 mmol) in 1,4-dioxane (8.0 mL) and water (4.0 mL) was stirred at 90° C. for 4 hours. After allowing to cool, the reaction solution was subjected to extraction with ethyl acetate (50 mL), and the organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with column chromatography (hexane/ethyl acetate=2:1) to yield the title compound (347.3 mg, 99%) as a colorless oil.

Workup

  1. temperatureto cool
  2. extractionthe reaction solution was subjected to extraction with ethyl acetate (50 mL)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with column chromatography (hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a2886c9988c84bbdb38491393b784dcc
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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