2-(2Indenyl)indole → HCID 57159028, compound

HRID 2392698Notes

Reaction equation

HRID 2392698 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:19](/[CH:21]=[CH:22]\[C:23]([O:25]CC)=O)#[N:20]>FC(F)(F)C(O)=O>[CH:5]1[C:4]2[CH2:3][C:2]3[C:10]4[NH:11][C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:18]=4[C:21]4=[CH:22][C:23](=[O:25])[N:20]=[C:19]4[C:1]=3[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 105856192-(2Indenyl)indoleHCID 15577688Ethyl (2Z)-3-cyanoprop-2-enoate

Product 1

HCID 57159028HCID 57159028, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(2-indenyl)indole 4 (75 mg; 0.32 mmol) and ethyl cis-β-cyanoacrylate (81 mg; 0.64 mmol) in trifluoroacetic acid (1 mL) was heated in a sealed reaction vial at 120° C. for 1 h., followed by 4 h at 160° C. The mixture was evaporated at reduced pressure and the residue was triturated with ether. The resulting solid was chromatographed (silica gel; EtOAc: hexanes; 1:1) to give 12 mg (12%) of tan solid product; mp 275°-280° C., MS (ES+) 310 (M+). This compound showed identical spectral data as that prepared in Method A.

Workup

  1. customThe mixture was evaporated at reduced pressure
  2. customthe residue was triturated with ether
  3. customThe resulting solid was chromatographed (silica gel; EtOAc: hexanes; 1:1)

Sources & evidence

ORD record
ord-729a07f3ca8747f080eca55c0602b4ae
Source dataset
uspto-grants-1998_09
Patent number
US05801190

Reaction notes

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