ethyl 2-methyl-1H-indole-3-carboxylate → HCID 59589494, compound

HRID 1501278

Reaction equation

HRID 1501278 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8]C=CC=2.[CH3:16][Al](C)C>O1CCOCC1>[CH3:8][C:9]1[CH:4]=[N:3][CH:16]=[C:2]([CH3:1])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 4072358ethyl 2-methyl-1H-indole-3-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 59589494HCID 59589494, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-methyl-1H-indole-3-carboxylate (2 g, 6.15 mmol), Pd(PPh3)-4(0.36 g, 0.31 mmol) in dioxane (20 mL) was added Me3Al (2 M in THF, 7.69 ml, 15.37 mmol) under N2. The mixture was stirred at reflux overnight. After the complete of the reaction, the reaction was quenched by addition of 5 mL of water and extracted with EtOAc. The extractions were combined, washed with H2O, dried over Na2SO4, and concentrated under vacuum. The residue was purified by flash column (Eluent: PE/EtOAc=15:1) to give ethyl 3,5-dimethylisonicotinate as a yellow solid. (0.9 g, yield 78%). LRMS (M+H+) m/z: calcd 180.2. found 179.01.

Workup

  1. temperatureat reflux overnight
  2. customAfter the complete of the reaction
  3. customthe reaction was quenched by addition of 5 mL of water
  4. extractionextracted with EtOAc
  5. extractionThe extractions
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column (Eluent: PE/EtOAc=15:1)

Sources & evidence

ORD record
ord-b0c87a855d0d494ea0b12b5a0b86bb7f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Linked notes

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