Methyl iodide → methyl 1H-indole-5-carboxylate

HRID 2170603Notes

Reaction equation

HRID 2170603 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N12CCCN=C1CCCC[CH2:14]2.IC>C(#N)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:14])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 742801H-Indole-5-Carboxylic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 2737635methyl 1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1H-indole-5-carboxylic acid (1 g, 6.2 mmol, 1.0 equiv) in acetonitrile (40 mL) were added 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.1 mL, 7.4 mmol, 1.2 equiv) and iodomethane (2.3 mL, 37.2 mmol, 6 equiv). The solution was stirred under reflux overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in AcOEt, washed with a 0.5 N HCl aqueous solution, a saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. The obtained oil was used in the next step without further purification.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washwashed with a 0.5 N HCl aqueous solution
  5. dry with materiala saturated NaHCO3 solution and brine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe obtained oil was used in the next step without further purification

Sources & evidence

ORD record
ord-49572d010f2544ff8f10f493c0c3d535
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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