Cesium carbonate → HCID 84038454, compound

HRID 1483168Notes

Reaction equation

HRID 1483168 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][C:2]2=[O:7])=[N:10][CH:11]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 669533-MorpholinoneHCID 693532,5-Dibromopyridine

Product 1

HCID 84038454HCID 84038454, compoundYield 64.2%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Morpholin-3-one (500 mg, 4.94 mmol) and 2,5-dibromopyridine (1.76 g, 7.42 mmol) were dissolved in toluene, to which was added cesium carbonate (2.42 g, 7.42 mmol). The resulting mixture was flushed with argon for 3 times. Then Pd2(dba)3 (226 mg, 0.247 mmol) and xantphos (171 mg, 0.296 mmol) were added, followed by flushing again with argon. The reaction mixture was heated to 100° C. and allowed to react overnight. After the reaction completed, the mixture was filtered. Column chromatography afforded 815 mg of white solid (compound 19a), yield 64%.

Workup

  1. customThe resulting mixture was flushed with argon for 3 times
  2. customby flushing again with argon
  3. customto react overnight
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-9c22865dd820476db9294f18c4b07eaf
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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