Potassium Cyanide → HCID 86703304, compound

HRID 2409987Notes

Reaction equation

Br[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=1.[C-:27]#[N:28].[K+]>O.C(O)C.O1CCCC1>[CH3:20][O:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([CH2:9][C:7]3[N:8]=[C:3]([CH2:2][C:27]#[N:28])[CH:4]=[CH:5][CH:6]=3)=[C:11]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:12]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-[6-(bromomethyl)pyridin-2-ylmethyl]-6-methoxy-2-phenyl-1H-indole (1.37 g) in water/ethanol/tetrahydrofuran (4 mL/16 mL/4 mL) was added potassium cyanide (263 mg), and the mixture was stirred at 80° C. for 13.5 hours. The reaction mixture was left to be cooled and concentrated under reduced pressure. To the residue was added water, followed by extraction with dichloromethane. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.05 g). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 3.95 (2H, s), 4.39 (2H, s), 6.76 (1H, dd, J=2.3, 8.5 Hz), 6.91 (1H, d, J=2.3 Hz), 7.04 (1H, d, J=7.8 Hz), 7.23 (1H, d, J=7.5 Hz), 7.30-7.39 (2H, m), 7.39-7.49 (2H, m), 7.50-7.61 (3H, m), 8.05 (1H, br s).

Workup

waitThe reaction mixture was left
temperatureto be cooled
concentrationconcentrated under reduced pressure
additionTo the residue was added water
extractionfollowed by extraction with dichloromethane
concentrationThe organic layer was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record: ord-814804ebc6814fb19737e051d4706e6b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815903B2

Reaction notes

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