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Isopropyl iodide → Methyl 1-isopropyl-1H-indole-6-carboxylate

HRID 1510129
Notes
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Reaction equation

HRID 1510129 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.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:21]([CH3:23])[CH3:22]>CN1C(=O)N(C)CCC1>[CH: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)([CH3:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 10608809Methyl 1-isopropyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 1H-indole-6-carboxylate (5.00 g, 28.5 mmol) and cesium carbonate (18.6 g, 57.1 mmol) in DMPU (50 mL) was added 2-iodopropane (3.71 mL, 37.1 mmol). After stirring at 80° C. for 4 h, the solution was cooled to rt, poured onto ether, washed with H2O (three times) and brine, dried with Na2SO4, and concentrated. The crude compound was chromatographed to give the desired product. LCMS (M+1)=218.1

Workup

  1. temperaturethe solution was cooled to rt
  2. additionpoured onto ether
  3. washwashed with H2O (three times) and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe crude compound was chromatographed

Sources & evidence

ORD record
ord-e30cd19d858c490c8254468f5d04a8a9
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08211904B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes