Phenanthridine → HCID 86602190, compound

HRID 1178750Notes

Reaction equation

HRID 1178750 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.[F:15][C:16]([F:31])([F:30])[C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20](Cl)=[O:21].[Si]([O:39][C:40]([O:42][CH3:43])=[CH2:41])(C(C)(C)C)(C)C>>[CH3:43][O:42][C:40](=[O:39])[CH2:41][CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[N:6]1[C:20](=[O:21])[C:19]1[CH:18]=[C:17]([C:16]([F:31])([F:30])[F:15])[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=1

Participants

4

Reactant 3

HCID 9189PhenanthridineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyethene

Product 1

HCID 86602190HCID 86602190, compound

Procedure

[5-(3,5-Bis-trifluoromethyl-benzoyl)-5,6-dihydro-phenanthridin-6-yl]-acetic acid methyl ester was prepared from phenanthridine, 3,5-bis(trifluoromethyl)benzoyl chloride, and 1-(tert-butyldimethylsilyloxy)-1-methoxyethene according to GP 2. Yield, 49%. 1H-NMR (DMSO-d6): δ=2.46 (dd, J=14.5 Hz, J=7.0 Hz, 1H), 2.57 (dd, J=14.5 Hz, J=7.8 Hz, 1H), 3.57 (s, 3H), 6.03 (s, br., 1H), 6.80 (s, br., 1H), 7.12 (s, br., 1H), 7.31 (t, J=7.6 Hz, 1H), 7.36-7.44 (m, 2H), 7.46-7.53 (m, 1H), 7.80 (s, br., 2H), 8.03 (dd, J=7.9 Hz, J=1.1 Hz, 1H), 8.07 (d, J=7.8 Hz, 1H), 8.20 (s, br., 1H); (+)-ESI-MS: m/z=494 [M+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-704fdb80d53044a6aeb6f80a66a89a3d
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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