Ethyl Bromide → HCID 21250523, compound

HRID 1531808Notes

Reaction equation

HRID 1531808 reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][C:4]=1[C:14]([OH:16])=[O:15])C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH3:25].I[CH2:27][CH3:28]>C(#N)C.C(OCC)(=O)C>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:27][CH3:28])[C:4]([C:14]([O:16][CH2:24][CH3:25])=[O:15])=[CH:3]2)#[N:13]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70239045HCID 70239045, compound

Product 1

HCID 21250523HCID 21250523, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2 Ethylcarboxy-5-cyanoindole (497 mg) [Liebigs Ann Chem, (3), 438-55 (1986)] and potassium carbonate (960 mg) were mixed in acetonitrile (25 ml) and bromoethane (191 μl) added. The reaction mixture was stirred for 18 hrs at 80° C. under a atmosphere of nitrogen. Iodoethane (200 μl) was added and the reaction mixture heated to 60° C. for 18 hrs after which time the mixture was diluted with ethyl acetate (100 ml) and washed with water, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with Hexane/Isopropanol/ 0.88 ammonium hydroxide (95/5/0.25, v/v) to afford the title compound as a white solid (455 mg).

Workup

  1. temperaturethe reaction mixture heated to 60° C. for 18 hrs after which time the mixture
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel eluting with Hexane/Isopropanol/ 0.88 ammonium hydroxide (95/5/0.25, v/v)

Sources & evidence

ORD record
ord-4124d54a0678408e8cad4919bd4240b4
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

Loading…