Triethylamine → N-(1H-indol-5-yl)pivalamide

HRID 1467959Notes

Reaction equation

HRID 1467959 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.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 788675-Aminoindole

Product 1

HCID 11171956N-(1H-indol-5-yl)pivalamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-Indole amine (0.6 g, 4.54 mmol) in anhydrous dichloromethane (15 mL), triethylamine (1.3 mL, 9.0 mmol) and pivaloyl chloride (0.45 mL, 5.4 mmol) were added and stirred at room temperature for 2 h. The reaction mixture was diluted with water; the organic layer was separated and concentrated in vacuo. The resultant residue was purified by flash column chromatography to give N-(1H-indol-5-yl)pivalamide (0.88 g, 89%); MS: 217.0 (M+1).

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4234786988214713881567e1171ac7a3
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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