2-(pyridin-3-yl)-1H-indole → 3-(3-Methoxycarbonylprop-2-ynyl)-2-(3-pyridyl)indole

HRID 1980875Notes

Reaction equation

HRID 1980875 reaction equation
C([Mg]Br)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=1.Br[CH2:21][C:22]#[C:23][C:24]([O:26][CH3:27])=[O:25]>O1CCCC1>[CH3:27][O:26][C:24]([C:23]#[C:22][CH2:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1)=[O:25]

Participants

5

Reactant 3

HCID 6066772-(pyridin-3-yl)-1H-indoleHCID 11469387Methyl 4-bromobut-2-ynoateHCID 178418443HCID 178418443, compound

Product 1

HCID 204008033-(3-Methoxycarbonylprop-2-ynyl)-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 30 ml of 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0°-5° is added dropwise over 30 minutes a solution of 10.0 g of 2-(3-pyridyl)indole in 60 ml of tetrahydrofuran. The mixture is stirred fo 0.5 hour at 0°-5° followed by the dropwise addition of 10.6 g of methyl bromotetrolate (J. Chem. Soc. 1950, 3646) in50 ml of tetrahydrofuran. The mixture is stirred for an additional 2 hours, at 0° poured into ice water, and extracted with ether. The aqueous phase is extracted with ether. The ether extract is washed with water, brine, and dried over anhydrous magnesium sulfate. Concentration in vacuo yields 3-(3-methoxycarbonyl-prop-2-ynyl)-2-(3-pyridyl)indole.

Workup

  1. stirringThe mixture is stirred for an additional 2 hours, at 0°
  2. extractionextracted with ether
  3. extractionThe aqueous phase is extracted with ether
  4. extractionThe ether extract
  5. washis washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a891379242734506b8de0964806fd891
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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