Diethylamine → 1H-Indolamine

HRID 966482Notes

Reaction equation

HRID 966482 reaction equation
C([NH:3]CC)C.C(OC([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22](CCOS(C)(=O)=O)[CH:23]=2)[NH:18][C:17]=1C(F)(F)F)=O)C1C=CC=CC=1>>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[C:17]1[NH2:3]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 233938765-(2-Methanesulfonyloxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 1220741H-IndolamineYield 20%

Procedure

Diethylamine (0.48 mL, 4.63 mmol, 3 eq) was added into the crude 5-(2-Methanesulfonyloxy-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic acid benzyl ester in dioxanes (20 mL) solution. The reaction mixture was heated to reflux overnight. After the solvent was removed, the residue was purified by gravity chromatography (SiO2, ethyl acetate-methanol-NH4OH) to yield the desire indole amine as pale yellow gel (20.0% yield). Elemental Analysis: C23H25F3N2O2.HCl: Calcd: C: 60.73; H: 5.76; N: 6.16. Found: C: 60.40; H: 5.83; N: 6.06. ESI-MS: m/z 419.73 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customAfter the solvent was removed
  4. customthe residue was purified by gravity chromatography (SiO2, ethyl acetate-methanol-NH4OH)

Sources & evidence

ORD record
ord-43c09ca90268469c99bbc5b4ea19033f
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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