Triethylamine → N-[(Indol-7-yl)methyl]-2-bromopropionamide

HRID 557218Notes

Reaction equation

HRID 557218 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][NH2:17])[CH:9]=[CH:8]1.C(N(CC)CC)C>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][NH:17][C:3](=[O:4])[CH:2]([Br:1])[CH3:6])[CH:9]=[CH:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 979802-Bromopropanoyl chlorideHCID 21950026(1H-Indol-7-YL)methanamine

Product 1

HCID 17985781N-[(Indol-7-yl)methyl]-2-bromopropionamideYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2-bromopropionyl chloride to a solution of (indol-7-yl)methylamine and triethylamine (0.49 g, 47.6 mmol) in tetrahydrofuran (20 ml) at 0° C. Stir for 1 hour at room temperature and quench with saturated aqueous sodium bicarbonate. Extract with ethyl acetate, concentrate under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound (0.62 g, 46%) as a yellow solid.

Workup

  1. customquench with saturated aqueous sodium bicarbonate
  2. extractionExtract with ethyl acetate
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-c86ed1f295b845d2a32f6a7aa3f9b69c
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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