Diethyl Ether → Ethyl 3-(5-cyano-1H-indol-1-yl)propanoate

HRID 423331Notes

Reaction equation

HRID 423331 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C>CN(C=O)C>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=[CH:3]2)#[N:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 27513Indole-5-carbonitrileHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 59318415Ethyl 3-(5-cyano-1H-indol-1-yl)propanoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1H-indole-5-carbonitrile (1.42 g, 10 mmol), ethyl 3-bromopropanoate (1.92 ml, 15 mmol) and cesium carbonate (6.5 g, 20 mmol) in DMF (50 ml) was heated at 80° C. for 4 hours. Cooled the solution, added diethyl ether (300 ml) and washed with water (3×300 ml). Dried over MgSO4 and evaporated off the solvent to yield 2.4 g of pale orange oil. This crude product was used in the next stage (preparation of D52).

Workup

  1. temperatureCooled the solution
  2. washwashed with water (3×300 ml)
  3. dry with materialDried over MgSO4
  4. customevaporated off the solvent

Sources & evidence

ORD record
ord-a06fb276966b4ab7928901557f6be0ca
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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