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

HRID 14225

Reaction equation

HRID 14225 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-32acb31f6e0644ba9d336afcf69903fe
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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