Indole → HCID 68489949, compound

HRID 1178718Notes

Reaction equation

HRID 1178718 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.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[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:21]([C:20]2[CH:24]=[CH:25][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[O:22])=[CH:27]1

Participants

4

Reactant 3

HCID 798IndoleHCID 7477p-Anisoyl chlorideHCID 9189Phenanthridine

Product 1

HCID 68489949HCID 68489949, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(4-methoxy-phenyl)-methanone was prepared from phenanthridine, 4-methoxybenzoyl chloride, and indole according to GP 2. Yield, 67%. 1H-NMR (DMSO-d6): δ=3.72 (s, 3H), 6.20 (dd, J=2.5 Hz, J=0.8 Hz, 1H), 6.39 (d, br., J=8 Hz, 1H), 6.81 (d, J=9.0 Hz, 2H), 6.81-6.88 (m, 1H), 6.98-7.08 (m, 2H), 7.12 (ddd, J=J=7.5 Hz, J=1.2 Hz, 1H), 7.15-7.26 (m, 2H), 7.18 (d, J=9.0 Hz, 2H), 7.42 (ddd, J=J=7.4 Hz, J=1.2 Hz, 1H), 7.53 (“t”, J≈7 Hz, 2H), 7.90 (“d”, J≈7 Hz, 1H), 7.95 (dd, J=7.9 Hz, J=1.3 Hz, 1H), 8.09 (“d”, J≈8 Hz, 1H), 10.68 (s, 1H); (+)-ESI-MS: m/z=431 [M+H]+, 314 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-8ce14dbd49ea454ab6f35e614be2bacd
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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