Allyl bromide → HCID 118274153, compound

HRID 522234Notes

Reaction equation

HRID 522234 reaction equation
[CH2:1]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[C:2]#[CH:3].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16](Br)[CH:17]=[CH2:18]>CN(C)C=O>[CH2:18]([N:5]1[C@H:4]([CH2:1][C:2]#[CH:3])[CH2:8][O:7][C:6]1=[O:9])[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 118274249HCID 118274249, compound

Product 1

HCID 118274153HCID 118274153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled suspension of Example 153B (1 g, 7.99 mmol) and Cs2CO3 (3.91 g, 11.99 mmol) in N,N-dimethylformamide (10 mL) was added dropwise allyl bromide (1.06 g, 8.79 mmol), and the reaction was stirred at room temperature overnight. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (3×40 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated to give the title compound which was used without further purification. MS (ESI+) m/z 166.0 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (3×40 mL)
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-271c78b4884a4aa6a7c8f417fd54003c
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

Loading…