2-Chloro-4-cyanopyridine → 2-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbonitrile

HRID 2277472Notes

Reaction equation

HRID 2277472 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=1)CCC>>[C:33]1([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:18]2[CH:19]=[C:15]([C:2]3[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=3)[N:16]=[CH:17]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 118281174-(Tributylstannyl)-1-tritylimidazole

Product 1

HCID 904076602-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbonitrileYield 77%

Procedure

The title compound was prepared in 77% yield from 2-chloro-4-pyridinenitrile and 4-(tributylstannyl)-1-tritylimidazole according to the procedure for Example 1, part A. 1H NMR (400 MHz, DMSO-d6): δ 7.17 (5H, m), 7.40-7.47 (10H, m), 7.49 (1H, d, J=1.2 Hz), 7.62 (1H, d, J=1.3 Hz), 7.65 (1H, dd, J=1.5 Hz and 5.0 Hz), 8.13 (1H, s), 8.67 (1H, d, 5.0 Hz).

Sources & evidence

ORD record
ord-a59fac35261b4e5c8949b3bb35a5d664
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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