Cesium carbonate → HCID 86673914, compound

HRID 1887483Notes

Reaction equation

HRID 1887483 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.Br[CH2:15][CH2:16][CH:17]=[CH2:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:18]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:12])([F:13])[F:1])=[CH:10][CH:9]=1)[CH2:17][CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21241Homoallyl bromideHCID 27771194-(2,2,2-Trifluoroethoxy)aniline

Product 1

HCID 86673914HCID 86673914, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 4-(2,2,2-Trifluoro-ethoxy)-phenylamine (2.5 g, 13 mmol), 4-bromobut-1-ene (3.54 g, 26 mmol) and Cs2CO3 (6.41 g, 20 mmol) was stirred in 30 mL of DMF at ambient temperature for 72 h. And then the mixture was filtered and washed with water. The filtrate was extracted with EtOAc (30 mL×3). The combined organic layers was washed with brine and dried with anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=30:1). The title compound (0.7 g, 22%) as brown oil was obtained. LC-MS: 246.1 [M+1]+.

Workup

  1. filtrationAnd then the mixture was filtered
  2. washwashed with water
  3. extractionThe filtrate was extracted with EtOAc (30 mL×3)
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-750308ff4d0c454e89228be61ac2dd5a
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

Loading…