Indole → HCID 68491463, compound

HRID 1178736Notes

Reaction equation

HRID 1178736 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[N:6]2[C:15](=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:27]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 69819Nonanoyl chloride

Product 1

HCID 68491463HCID 68491463, compound

Procedure

1-[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-nonan-1-one was prepared from phenanthridine, pelargonyl chloride, and indole according to GP 2. Yield, 2%. 1H-NMR (DMSO-d6): δ=0.81 (t, J=7.0 Hz, 3H), 0.99-1.24 (m, 10H), 1.44-1.58 (m, 2H), 2.30-2.75 (m, 2H; overlap with solvent signal), 6.08 (s, br., 1H), 6.98 (td, J=7.4 Hz, 1H), 7.04 (td, J=7.4 Hz, 1H), 7.10-7.19 (m, 2H), 7.20-7.33 (m, 3H), 7.38 (td, J=7.3 Hz, J=1.0 Hz, 1H), 7.43-7.51 (m, 2H), 7.69 (d, J=7.5 Hz, 1H), 7.94 (d, J=7.6 Hz, 1H), 8.00 (d, J=7.4 Hz, 1H), 10.62 (s, 1H); (+)-ESI-MS: m/z=437 [M+H]+, 320 [M-indole+H]+, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-d856f90c485e4a6883e3c6bab3e0dc5b
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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