Water → Ethyl 1-(4-fluorobenzyl)-1H-indole-2-carboxylate

HRID 83590Notes

Reaction equation

HRID 83590 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 69873711Ethyl 1-(4-fluorobenzyl)-1H-indole-2-carboxylateYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1H-indole-2-carboxylate (500 mg, 2.64 mmol) was dissolved in anhydrous DMF (8 ml), followed by 1-(chloromethyl)-4-fluorobenzene (0.380 ml, 3.17 mmol) and the addition of solid potassium carbonate (730 mg, 5.29 mmol). This was stirred at 60° C. for 20 h, at which time the reaction was allowed to cool to room temperature. Precipitate formed upon the addition of water (40 mL), was isolated over a filter, and dried under high vacuum overnight to give 550 mg of the title compound as a white solid which was recrystallized from diethyl ether. Rf=0.55 (33% EtOAc/Hex.)

Workup

  1. temperatureto cool to room temperature
  2. customwas isolated over a filter
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-823d6a94b97e476ea59b996afb12f604
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

Loading…