Triethylamine → 1H-indole-6-carbonitrile

Temperature

50 °C

2-Chloro-1-methylpyridium iodide (1.316 g) was added to a solution of 1H-indole-6-carbaldehyde oxime (D11) (750 mg) in dry THF (80 mL) at RT. After stirring for 10 min, triethylamine (2.284 mL) was added to the reaction mixture. The reaction mixture was heated to 50° C. and stirred at 50° C. for 3.5 hours, then left overnight with stirring at RT. The mixture was heated to refluxed for 5 hours. The solvent was evaporated. The residue was dissolved in EtOAc (100 mL) and water (100 mL) was added. The organic fraction was separated. The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 1H-indole-6-carbonitrile (D12) as a brown solid (680 mg). δH (DMSO-d6, 400 MHz): 6.60 (1H, m), 7.32 (1H, dd), 7.68 (1H, m), 7.72 (1H, d), 7.88 (1H, m), 11.68 (1H, br s). MS (ES): C9H6N2 requires 142; found 141.0 (M−H+).

1. stirringstirred at 50° C. for 3.5 hours
2. waitleft overnight
3. stirringwith stirring at RT
4. temperatureThe mixture was heated
5. temperatureto refluxed for 5 hours
6. customThe solvent was evaporated
7. dissolutionThe residue was dissolved in EtOAc (100 mL)
8. additionwater (100 mL) was added
9. customThe organic fraction was separated
10. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
11. concentrationThe dried solution was concentrated

ORD record

ord-60c51e81a786464589b2a9931d9c3fc5

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217028B2