1,5-Bis(2-pyridyl)-1,3,5-pentanetrione → 4,4''-diethoxy-1'H-[2,2';6',2'']terpyridin-4'-one

HRID 273310Notes

Reaction equation

HRID 273310 reaction equation
[N:1]1C=CC=CC=1C(=O)CC(=O)CC(C1C=CC=CN=1)=O.[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30](=O)[CH2:31][C:32](=[O:45])[CH2:33][C:34]([C:36]2[CH:41]=[C:40]([O:42][CH2:43][CH3:44])[CH:39]=[CH:38][N:37]=2)=O)[CH:25]=1)[CH3:22]>>[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]2[NH:1][C:34]([C:36]3[CH:41]=[C:40]([O:42][CH2:43][CH3:44])[CH:39]=[CH:38][N:37]=3)=[CH:33][C:32](=[O:45])[CH:31]=2)[CH:25]=1)[CH3:22]

Participants

3

Reactant 2

HCID 113691811,5-Bis(2-pyridyl)-1,3,5-pentanetrioneHCID 179719321,5-Bis(4-ethoxy-pyridin-2-yl)pentane-1,3,5-trione

Product 1

HCID 587814364,4''-diethoxy-1'H-[2,2';6',2'']terpyridin-4'-one

Procedure

This compound is prepared in a manner analogous to that described in Example 1, Step 2 for 1,5-di-pyridin-2-yl-pentane-1,3,5-trione, but instead the ethoxy-substituted triketone from Example 20 is used. Pure 4,4″-diethoxy-1′H-[2,2′;6′,2″]terpyridin-4′-one can be obtained by chromatography on silica gel (chloroform/methanol 9:1, 0.1% NH4OH) in the form of a white crystalline powder. 1H-NMR (360 MHz, CDCl3): 1.37 (t, 6H, 7.2 Hz); 4.05 (q, 4H, 7.2 Hz); 6.77 (dd, 2H, J=5.9, 2.3 Hz), 6.99 (br s, 2H), 7.30 (br s, 2H); 8.42 (d, 2H, J=5.9 Hz). MS (EI pos., 70 eV), m/z=337 (75, [M+]); 322 (90); 309 (100); 281 (75); 28 (85).

Workup

  1. customThis compound is prepared in a manner analogous to

Sources & evidence

ORD record
ord-c328c890a8944cf09351aec6cc146eb7
Source dataset
uspto-grants-2008_11
Patent number
US07456285B2

Reaction notes

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