Cesium carbonate → HCID 58007530, compound

HRID 1094361Notes

Reaction equation

HRID 1094361 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][NH2:15].I[C:17]1[CH:18]=[C:19]([CH3:24])[C:20]([CH3:23])=[CH:21][CH:22]=1.C(C1CCCCC1=O)(=O)C>CN(C=O)C.O.[Cu]I>[CH3:24][C:19]1[CH:18]=[C:17]([NH:15][CH2:14][CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=2)[CH:22]=[CH:21][C:20]=1[CH3:23]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 134002-AcetylcyclohexanoneHCID 759192-PyridineethanamineHCID 1416464-Iodo-1,2-dimethylbenzene

Product 1

HCID 58007530HCID 58007530, compoundYield 31.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A dried flask was charged with 21 mg (0.11 mmol) CuI and 1.4 g (4.3 mmol) cesium carbonate under argon. 0.31 g (2.6 mmol) 2-pyridin-2-yl-ethylamine (CAS: 2706-56-1), 0.5 g (2.1 mmol) 4-iodo-0-xylene in solution in 1 mL dried DMF and finally 0.058 mL (0.43 mmol) 2-acetylcyclohexanone were successively added. The mixture was stirred at room temperature for 17 hours and then in a 65° C. oil-bath for 7 hours. The mixture was diluted with water. The aqueous layer was extracted twice with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.15 g (31%) of the title compound as a yellow oil. MS (m/e): 227.2 [M+H]+.

Workup

  1. waitin a 65° C. oil-bath for 7 hours
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  7. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-9417b52f0ce4465a8d8a80ac2b0a7221
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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