Butyl iodide → butyl 1-butyl-1H-indole-6-carboxylate

HRID 349015

Reaction equation

HRID 349015 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].I[CH2:24][CH2:25][CH2:26][CH3:27]>CS(C)=O.[Cl-].[Na+].O.O.C(OCC)(=O)C>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:24][CH2:25][CH2:26][CH3:27])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 3

HCID 10962Butyl iodideHCID 210851671-butyl-1H-indole-6-carboxylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 21086016butyl 1-butyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1-Butyl-1H-indole-6-carboxylic acid (0.450 g) was dissolved in dimethyl sulfoxide (10 mL). Potassium tert-butoxide (0.317 g) was added and the mixture was stirred for 10 min at room temperature. Iodobutane (0.33 mL) was added and the mixture was allowed to stir at room temperature for 6 h. Water was then added and the mixture was partioned between ethyl acetate, water, and brine, and dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography using heptane/dichloromethane (30/70) gave butyl 1-butyl-1H-indole-6-carboxylate (0.429 g). MS (ESI+) for C17H23NO2+H1 m/z 274.20 (M+H)+.

Workup

  1. stirringto stir at room temperature for 6 h
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d1dcf4bd7a04dd18dd0ff98536db774
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

Loading…