Indole → HCID 23118672, compound

HRID 1178741Notes

Reaction equation

HRID 1178741 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.[CH:15]1([CH2:21][CH2:22][C:23](Cl)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[CH:15]1([CH2:21][CH2:22][C:23]([N:6]2[CH:7]([C:28]3[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:26][CH:27]=3)[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]2=3)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 2734098Cyclohexylpropionyl chloride

Product 1

HCID 23118672HCID 23118672, compound

Procedure

3-Cyclohexyl-1-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-propan-1-one was prepared from phenanthridine, 3-cyclohexylpropionyl chloride, and indole according to GP 2. Yield, 5.5%. 1H-NMR (CD3OD): δ=0.56-0.79 (m, 2H), 0.86-1.09 (m, 4H), 1.26-1.62 (m, 7H), 2.47-2.70 (m, 2H), 6.08 (s, 1H), 6.96-7.05 (m, 2H), 7.07 (td, J=7.2 Hz, J=1.3 Hz, 1H), 7.13 (td, J=7.9 Hz, J=1.4 Hz, 1H), 7.21 (“d”, J≈7.4 Hz, 1H), 7.27 (“t”, J≈7.6 Hz, 1H), 7.36-7.42 (m, 3H), 7.46-7.53 (m, 1H), 7.78 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.6 Hz, 1H), 7.98 (d, J=7.7 Hz, 1H); (+)-ESI-MS: m/z=435 [M+H]+, 318 [M-indole+H]+, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-93926c44d5aa4e31826238d1ada85c9c
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

Loading…