Methyl iodide → 4'-Methoxy-4,4''-di-pyrrolidin-1-yl-[2,2';6',2'']-terpyridine

HRID 640674Notes

Reaction equation

[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[NH:15][C:16]([C:21]4[CH:26]=[C:25]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)[CH:24]=[CH:23][N:22]=4)=[CH:17][C:18](=[O:20])[CH:19]=3)[CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:32]I>CN(C)C=O>[CH3:32][O:20][C:18]1[CH:17]=[C:16]([C:21]2[CH:26]=[C:25]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH:24]=[CH:23][N:22]=2)[N:15]=[C:14]([C:10]2[CH:9]=[C:8]([N:3]3[CH2:4][CH2:5][CH2:6][CH2:7]3)[CH:13]=[CH:12][N:11]=2)[CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

26 mg of sodium hydride dispersion (60% strength, 0.65 mmol) are suspended under argon in 5 ml of abs. N,N-dimethylformamide and cooled to 0° C. Then 193 mg (0.5 mmol) of 4,4″-di-pyrrolidin-1-yl-1′H-[2,2′;6′,2″]terpyridin-4′-one (L18 from Example 24) are added. The yellow suspension is stirred for 30 minutes 0° C. and then heated at room temperature for 15 minutes. The mixture is cooled again and a solution of 40 μl (0.65 mmol) of methyl iodide is added. The mixture is stirred for a further 45 minutes and the precipitate that forms is filtered off and recrystallised from methanol. 4′-Methoxy-4,4″-di-pyrrolidin-1-yl-[2,2′;6′,2″]-terpyridine is obtained in the form of a white solid. 168.1 (quart.); 157.9 (quart.); 156.6 (quart.); 152.9 (quart.); 149.5 (tert.); 107.4 (tert.); 107.1 (tert.); 105.0 (tert.); 55.9 (prim.); 47.3 (sec.); 25.8 (sec.). MS (EI, 70 eV), m/z: 401 (50, [M+]); 373 (80); 372 (100); 332 (20); 28 (40).

Workup

temperatureheated at room temperature for 15 minutes
temperatureThe mixture is cooled again
stirringThe mixture is stirred for a further 45 minutes
filtrationthe precipitate that forms is filtered off
customrecrystallised from methanol

Sources & evidence

ORD record: ord-9520d7f3bcd6474fbf86911d46285708
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692004B2

Reaction notes

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