Triethylamine → HCID 22611347, compound

HRID 1737708Notes

Reaction equation

HRID 1737708 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1.Cl>[CH2:22]([O:21][C:19]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 788675-Aminoindole

Product 1

HCID 22611347HCID 22611347, compoundYield 112.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.27 gm (32.3 mMol) 5-amino-1H-indole in 50 mL tetrahydrofuran were added 5.4 ML (38.8 mMol) triethylamine and the reaction mixture was then cooled to 0° C. To this solution were then added dropwise 3.4 mL (35.5 mMol) ethyl chloroformate. After 4 hours the reaction mixture was diluted with 1N HCl and was then extracted with ethyl acetate. The organic phase was washed sequentially with 1N HCl, water and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure to give 7.4 gm of a dark oil. This oil was purified by flash chromatography, eluting with a gradient of dichloromethane containing 0-2.5% methanol, to give 4.95 gm (75%) of the title compound as a tan solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic phase was washed sequentially with 1N HCl, water and saturated aqueous sodium chloride
  3. dry with materialThe remaining organics were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-049f2cb4c3af4dae840cde4783b3f91f
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

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