2-Cyclopenten-1-one → HCID 22139459, compound

HRID 1825716Notes

Reaction equation

HRID 1825716 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[N:8]>C(#N)C.O.O.O.O.O.O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[O:6]=[C:1]1[CH2:5][CH2:4][CH:3]([C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([C:7]#[N:8])[CH:10]=3)[NH:14][CH:13]=2)[CH2:2]1

Participants

5

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 27513Indole-5-carbonitrile

Product 1

HCID 22139459HCID 22139459, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 86591886HCID 86591886, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Cyclopenten-1-one (4.1 g, 4.2 mL, 50 mMol) was added to a stirred solution of 5-cyanoindole (1.42 g, 10 mMol) and ytterbium triflate hexahydrate (124 mg, 0.2 mMol) in acetonitrile (15 mL). After stirring at room temperature for 7d, the reaction was concentrated to an oil and diluted with ether. The red oily mixture was filtered through celite and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (35 g) using a gradient of 20–35% ethyl acetate in hexane. Pure product fractions were concentrated and dried under high vacuum to give 3-(3-oxocyclopentyl)-1H-indole-5-carbonitrile (1.55 g, 69%). 1H NMR (500 MHz, CDCl3) δ 8.41 (1 H, bs), 7.99 (1 H, s), 7.45 (2 H, m), 7.12 (1 H, dd, J=2.44, 0.92 Hz), 3.72 (1 H, m), 2.77 (1 H, dd, J=7.63, 18.31 Hz), 2.56 (1 H, m), 2.40 (3 H, m), 2.10 (1 H, m). MS m/e 223.2 (M−H)+. Anal. calcd. for C14H12N2O: C, 74.98; H, 5.39; N, 12.49. Found: C, 74.75; H, 5.50; N, 12.23.

Workup

  1. concentrationthe reaction was concentrated to an oil
  2. additiondiluted with ether
  3. filtrationThe red oily mixture was filtered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude product was purified by flash chromatography on silica gel (35 g)
  6. concentrationPure product fractions were concentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-7708e6ef646e42e689a8e0c5b3117bfa
Source dataset
uspto-grants-2006_05
Patent number
US07049314B2

Reaction notes

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