Potassium Carbonate → HCID 123339094, compound

HRID 920876Notes

Reaction equation

HRID 920876 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][CH:12]=[O:13])=[CH:2]1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Br.[OH-].[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[OH:18][CH2:17][CH2:16][CH2:14][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][CH:12]=[O:13])=[CH:2]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 18430EpibromohydrinHCID 540588453-(1H-Indol-3-yl)prop-2-enal

Product 1

HCID 123339094HCID 123339094, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 10 mL Pyrex-glass vessel is mixed 3-(1H-indol-3-yl)acrylaldehyde (171 mg, 1 mmol), epibromohydrin (137 mg, 1 mmol), KOH (224 mg, 4 mmol) and anhydrous K2CO3 (553 mg, 4 mmol) in 1 mL DMF. This mixture is subjected to microwave irradiation at 350 W in successive 30 s periods, with 30 s periods at room temperature between each irradiation to avoid overheating the reaction. After the reaction has reached completion as monitored by TLC (5:1-hexanes:EtOAc) the reaction mixture is allowed to cool to room temperature and then is quenched by the addition of 10 mL 1M NaOH under vigorous stirring. The mixture is stirred for an additional 2 hrs, whereupon it is poured into 50 mL of ice-cold water. The precipitated solids are removed by filtration and washed 3×25 mL with water. The resulting solids are dried under vacuum and then recrystallized from ethanol to afford colorless crystals.

Workup

  1. customirradiation at 350 W in successive 30 s periods
  2. customwith 30 s periods at room temperature between each irradiation
  3. customthe reaction
  4. customis quenched by the addition of 10 mL 1M NaOH under vigorous stirring
  5. additionis poured into 50 mL of ice-cold water
  6. customThe precipitated solids are removed by filtration
  7. washwashed 3×25 mL with water
  8. customThe resulting solids are dried under vacuum
  9. customrecrystallized from ethanol
  10. customto afford colorless crystals

Sources & evidence

ORD record
ord-a2fb3429f868445db192c6f5bb1eaac6
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

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