2-(pyridin-3-yl)-1H-indole → 3-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole

HRID 1980859Notes

Reaction equation

HRID 1980859 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][CH2:22][O:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>O1CCCC1>[CH2:31]([O:30][C:28]([C:27]1[CH:33]=[CH:34][C:24]([O:23][CH2:22][CH2:21][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)=[CH:25][CH:26]=1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 6066772-(pyridin-3-yl)-1H-indoleHCID 12708668Ethyl 4-(2-bromoethoxy)benzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 204007903-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 12.0 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0°-5° is added dropwise over 20 minutes a solution of 4.0 g of 2-(3-pyridyl)indole in 20 ml of tetrahydrofuran. The mixture is stirred for 0.5 hours at 0°-5° and then is added a solution of 5.06 g of ethyl p-(2-bromoethoxy)benzoate [for preparation see U.S. Pat. No. 2,790,825 (1957)] in 30 ml of tetrahydrofuran. The suspension is stirred at 0°-10° for 1 hour and at room temperature for 0.5 hour, poured into ice-water and extracted with ether. The ether extract is separated, dried over MgSO4, and concentrated to give 3-[2-(4-ethoxycarbonylphenoxy)-ethyl]-2-(3-pyridyl)-indole.

Workup

  1. customfor preparation
  2. stirringThe suspension is stirred at 0°-10° for 1 hour and at room temperature for 0.5 hour
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. customis separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-135efbcacef84bd1a9f20aea46b9162b
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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