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

HRID 349011

Reaction equation

HRID 349011 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].I[CH2:21][CH2:22][CH2:23][CH3:24]>CS(C)=O>[CH2:21]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 639844Methyl indole-6-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 1H-indole-6-carboxylate (4.17 g) was dissolved in DMSO (30 mL), and potassium tert-butoxide (2.93 g) was added. The mixture was stirred for ten min at room temperature. Iodobutane (3.0 mL) was added. The mixture was allowed to stir for three additional hours. The mixture was partitioned between ethyl acetate and water and brine, dried over sodium sulfate, filtered, and concentrated to give methyl 1-butyl-1H-indole-6-carboxylate (4.53 g). MS (ESI+) for C14H17NO2+H1 m/z 232.12 (M+H)+.

Workup

  1. stirringto stir for three additional hours
  2. customThe mixture was partitioned between ethyl acetate and water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ccf495f13d924e488b5095017a02e098
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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