Potassium Carbonate → HCID 77231201, compound

HRID 400728Notes

Reaction equation

HRID 400728 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2)#[N:11].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:16]=[CH:15]2)#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27513Indole-5-carbonitrileHCID 79177tert-Butyl bromoacetate

Product 1

HCID 77231201HCID 77231201, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl bromoacetate (0.88 mL; 5.99 mmol) was added to a suspension of 5-cyanoindole (0.71 g; 4.99 mmol) and K2CO3 (1.38 g; 9.99 mmol) in CH3CN (20 mL) and the resulting mixture was stirred at reflux for 16 hours. Filtration and concentration in vacuo gave a light yellow oil which crystallized upon standing. The solid was triturated in a mixture of Et2O and hexane to give the title compound as an off-white solid (1.26 g, 98%). HPLC (Method A), Rt: 4.43 min (Purity: 96.8%). LC/MS (Method B): 256.9 (M+H)+.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationFiltration and concentration in vacuo
  3. customgave a light yellow oil which
  4. customcrystallized
  5. customThe solid was triturated in a mixture of Et2O and hexane

Sources & evidence

ORD record
ord-b8c0bfe6716441c59b0e476b5a97cf28
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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