Ethyl Bromide → HCID 18765170, compound

HRID 1059711Notes

Reaction equation

HRID 1059711 reaction equation
[OH:1][C:2]1[C:3]([I:15])=[C:4]([C:7]([N+:12]([O-:14])=[O:13])=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].Br[CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:1][C:2]1[C:3]([I:15])=[C:4]([C:7]([N+:12]([O-:14])=[O:13])=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6])[CH3:18]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 18765173HCID 18765173, compound

Product 1

HCID 18765170HCID 18765170, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of step (a) (6.95 g, 21.7 mmol) and bromoethane (1.78 ml, 23.8 mmol) in DMF (70 ml) was added potassium carbonate (4.49 g, 32.5 mmol) and the reaction was heated to 60° C. for 18 h. After cooling, the reaction mixture was partitioned between 2N aqueous HCl and EtOAc, the organic layer was separated, washed with H2O, dried over MgSO4 and evaporated. The crude product was purified on silica gel, eluting with CH2Cl2/MeOH (97/3, v/v) to afford the subtitle compound as a colourless solid (2.94 g, 39%). Rf 0.68 (CH2Cl2/MeOH 95/5, v/v). MS m/z 366 (MNH4+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between 2N aqueous HCl and EtOAc
  3. customthe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe crude product was purified on silica gel
  8. washeluting with CH2Cl2/MeOH (97/3

Sources & evidence

ORD record
ord-9839095905e94c64848f4e989c159207
Source dataset
uspto-grants-2003_02
Patent number
US06521629B2

Reaction notes

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