Tetrahydrofuran → ethyl 3-(7-cyano-1H-indol-3-yl)propanoate

HRID 1512748Notes

Reaction equation

HRID 1512748 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]#[N:11])[CH:3]=[CH:2]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C1COCC1>ClCCCl.C(Cl)Cl>[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[C:3]2[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])#[N:11]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8821Ethyl Acrylate2×HCID 108988161H-Indole-7-carbonitrile2×

Product 1

HCID 59146022ethyl 3-(7-cyano-1H-indol-3-yl)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1H-indole-7-carbonitrile (D2) (3.0 g), FeCl3 (3.4 g) and ethyl acrylate (7.5 mL) in DCE (3 mL) was added into 4 tubes respectively. In the fifth tube was added a mixture of 1H-indole-7-carbonitrile (2.0 g), FeCl3 (2.3 g) and ethyl acrylate (5 mL) in DCE (2 mL). The tubes were sealed and heated at 120° C. for 2 hours. After cooling to room temperature, the combined mixture was diluted with DCM and a little amount of THF. The solid was filtered off through celite. The mixture was washed with 0.5 M HCl solution three times and then brine. The organic solution was dried over anhydrous sodium sulfate. After concentration, the residue was purified by flash chromatography to give Ethyl 3-(7-cyano-1H-indol-3-yl)propanoate (13.4 g). δH (CDCl3, 400 MHz): 1.23 (3H, t), 2.70 (2H, t), 3.10 (2H, t), 4.13 (2H, q), 7.16 (2H, m), 7.51 (1H, dd), 7.83 (1H, d), 8.88 (1H, br s).

Workup

  1. additionwas added into 4 tubes respectively
  2. additionIn the fifth tube was added
  3. customThe tubes were sealed
  4. temperatureAfter cooling to room temperature
  5. filtrationThe solid was filtered off through celite
  6. washThe mixture was washed with 0.5 M HCl solution three times
  7. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  8. concentrationAfter concentration
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-51237f8d80c046ef972c0191853bb899
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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