Cesium carbonate → 2-(3-Methylimidazol-4-yl)cyclohex-2-en-1-one

HRID 337789Notes

Reaction equation

HRID 337789 reaction equation
O=[C:2]1[C:7]([O:8]B(O)O)=[CH:6][CH2:5][CH2:4][CH2:3]1.Br[C:13]1[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>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>[CH3:18][N:17]1[C:13]([C:2]2[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=2)=[CH:14][N:15]=[CH:16]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 89963618(6-Oxocyclohex-1-en-1-yl)boric acid

Product 1

HCID 899632992-(3-Methylimidazol-4-yl)cyclohex-2-en-1-oneYield 8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 39a by using (6-oxocyclohex-1-en-1-yl)boric acid (J. Org. Chem. 2011, 76, 3946-3959; 790 mg, 5.65 mmol), 5-bromo-1-methyl-1H-imidazole (910 mg, 5.65 mmol), tetrakis(triphenylphosphine)palladium (0) (326 mg, 0.282 mmol), cesium carbonate (4.00 g, 12.3 mmol), 1,4-dioxane (10 mL) and water (5 mL), to yield the title compound (80 mg, 8%) as a brown oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-1e1ec7c9280b4b5896ec358aa5ab7569
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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