2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(1H-Indol-2-yl)quinoline

HRID 843276Notes

Reaction equation

N1C2C(=CC=CC=2)C=C1[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1.[NH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]C1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[NH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[C:11]1[CH:12]=[CH:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The indolyl-tetrahydroquinoline was made according to the established lanthanide triflate catalyzed Kobayashi chemistry (for a leading reference, see Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis, 1995, 1195-1202). The tetrahydroquinoline (50.0 mg, 0.102 mmol) was dissolved in 10 mL anhydrous dichloromethane and the solution was cooled to 0° C. under nitrogen atmosphere. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (47.6 mg, 0.210 mmol) in 2 mL dichloromethane was then added in a drop-wise fashion. The reaction mixture was stirred at 0° C. for additional 30 minutes. The reaction crude was filtered through celite and the solvent was evaporated in vacuo to supply a yellow solid. Further purification by flash column chromatography (alumina basic, CH2Cl2/MeOH=20:1) yielded 27.5 mg of indolyl-quinoline 517.

Workup

customSynthesis, 1995, 1195-1202)
customThe reaction crude
filtrationwas filtered through celite
customthe solvent was evaporated in vacuo to supply a yellow solid
customFurther purification by flash column chromatography (alumina basic, CH2Cl2/MeOH=20:1)

Sources & evidence

ORD record: ord-8cc20a2e19ce43f48019baaf7c361736
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376670B1

Reaction notes

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