Cesium carbonate → HCID 66778355, compound

HRID 2091394Notes

Reaction equation

HRID 2091394 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])=[C:7]([CH3:18])[C:6]=2[CH:19]=1.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:12]1([C:10]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([N:20]4[CH2:25][CH2:24][S:23][CH2:22][CH2:21]4)=[CH:19][C:6]=3[C:7]=2[CH3:18])=[O:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 67164ThiomorpholineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43805642HCID 43805642, compound

Product 1

HCID 66778355HCID 66778355, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution (15 mL) of (5-bromo-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methanone (0.75 g) synthesized in Example A174(1) in toluene were added thiomorpholine (0.72 g), cesium carbonate (2.3 g), tris(dibenzylideneacetone)dipalladium (0) (0.16 g) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.2 g), and the mixture was heated under reflux under argon atmosphere for 18 hr. The reaction mixture was cooled to room temperature and filtered through celite, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was concentrated to give a crude product (0.83 g, quantitative) of the title object compound as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere for 18 hr
  3. filtrationfiltered through celite, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-bf64024037d149ffa46948b4331e3a3c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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