Water → 4,4''-Diethoxy-4'-methoxy-[2,2';6',2'']terpyridine

HRID 640673Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[NH:11][C:12]([C:17]3[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[CH:20]=[CH:19][N:18]=3)=[CH:13][C:14](=[O:16])[CH:15]=2)[CH:5]=1)[CH3:2].[H-].[Na+].[CH3:28]I.O>CN(C)C=O>[CH2:24]([O:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([C:12]2[CH:13]=[C:14]([O:16][CH3:28])[CH:15]=[C:10]([C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][N:7]=3)[N:11]=2)[CH:22]=1)[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

In an argon atmosphere, 506 mg (1.5 mmol) of 4,4″-diethoxy-1′H-[2,2′;6′,2″]terpyridin-4′-one (L17, Example 23) are added at 0° C. to a suspension of 78 mg (approximately 60% dispersion in paraffin oil, 1.95 mmol) of sodium hydride in 15 ml of absolute N,N-dimethylformamide. The mixture is then stirred for 15 minutes at 0° C. and for 15 minutes at room temperature. After cooling again, 0.12 ml (1.95 mmol) of methyl iodide is added. Stirring is then carried out at room temperature for a further 45 minutes. 15 ml of water are added and filtration is carried out, yielding 4,4″-diethoxy-4′-methoxy-[2,2′;6′,2″]terpyridine in the form of a beige powder. 1H-NMR (360 MHz, CDCl3): 1.39 (t, 6 H, J=7.2 Hz); 3.90 (s, 3H); 4.12 (q, 4H, J=7.2 Hz); 6.73 (dd, 2H, J=5.6, 2.5 Hz); 7.88 (s, 2H); 8.01 (d, 2H, J=2.5 Hz); 8.39 (d, 2H, 5.6 Hz). MS (EI pos, 70 eV), m/z=351 (90, [M+]); 350 (70); 336 (100); 323 (70); 295 (45).

Workup

temperatureAfter cooling again
stirringStirring
waitis then carried out at room temperature for a further 45 minutes
filtrationfiltration

Sources & evidence

ORD record: ord-74e5e0bba7f647e39e675829d6852dd6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692004B2

Reaction notes

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