Cesium carbonate → HCID 86684065, compound

HRID 407804Notes

Reaction equation

HRID 407804 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][N:4]=[N:3]1.Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([Br:15])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].O1CCOCC1>[Br:15][C:13]1[CH:14]=[C:9]([NH:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][CH:5]=2)[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 127607171-Methyl-1H-1,2,3-triazol-5-amine

Product 1

HCID 86684065HCID 86684065, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (20 mL), 154a (500 mg, 5.10 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (1362 mg, 5.10 mmol), and cesium carbonate (3.325 g, 10.2 mmol). After bubbling nitrogen through the suspension for 20 minutes, Xantphos (0.59 g, 1.02 mmol) and tris(dibenzylideneacetone)dipalladium(0) (467 mg, 0.51 mmol) were added. The system was subjected to three cycles of vacuum/nitrogen flush and heated at reflux for 5 h. It was then cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 154b (220 mg, 15%) as a brown solid. LCMS: [M+H]+ 284.1

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter bubbling nitrogen through the suspension for 20 minutes
  3. customflush
  4. temperatureheated
  5. temperatureat reflux for 5 h
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customThe residue was purified by silica-gel column chromatography
  9. washeluting with 50:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-b9018a9a2c4947008d02f24ef61de9d0
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

Loading…