Triethylamine → ethyl 1H-indol-5-ylcarbamate

HRID 1467995Notes

Reaction equation

HRID 1467995 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH2:18]([O:20][C:21](Cl)=[O:22])[CH3:19]>ClCCl>[CH2:18]([O:20][C:21](=[O:22])[NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 788675-Aminoindole

Product 1

HCID 54033885ethyl 1H-indol-5-ylcarbamateYield 35.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1H-indol-5-amine (11 g, 83.2 mmol) and triethyl amine (25.22 g, 250 mmol) in dichloromethane (110 mL) at −10° C., ethyl-chloro-formate (13.5 g 124.8 mmol) was added dropwise and stirred at 0° C. for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to give ethyl-1H-indol-5-ylcarbamate (5.980 g, 35.2%); MS: 205 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-7af1d86742654a98bab712e45762843f
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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