Indole → HCID 68492239, compound

HRID 1178713Notes

Reaction equation

HRID 1178713 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:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25]1>>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([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]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:22])=[CH:25]1

Participants

4

Reactant 3

HCID 798IndoleHCID 7412Benzoyl chlorideHCID 9189Phenanthridine

Product 1

HCID 68492239HCID 68492239, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-phenyl-methanone was prepared from phenanthridine, benzoyl chloride, and indole according to GP 2. Yield, 11%. 1H-NMR (DMSO-d6): δ=6.20 (dd, J=2.5 Hz, J=0.8 Hz, 1H), 6.36 (s, br., 1H), 6,80 (t, J=7.6 Hz, 1H), 6.99-7.08 (m, 2H), 7.11 (ddd, J=J=7.5 Hz, J=1.2 Hz, 1H), 7.19-7.31 (m, 6H), 7.37 (“t”, J≈7.1 Hz, 1H), 7.43 (“t”, J≈7 Hz, 1H), 7.54 (“t”, J≈7 Hz, 2H), 7.85-7.90 (m, 1H), 7.95 (dd, J=7.8 Hz, J=1.2 Hz, 1H), 8.10 (“d”, J≈7.5 Hz, 1H), 10.69 (s, 1H); (+)-ESI-MS: m/z=401 [M+H]+, 284 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-1969b3702fdb419299ccf89d15eff6f4
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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