Imidazole → HCID 86680631, compound

HRID 1497466Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:13]([C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:14][CH3:15].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N:1]1([CH:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH2:29][CH2:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:14][CH3:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of imidazole (0.034 g, 0.332 mmol) in DMF (3 ml) was added potassium carbonate (0.11 g, 0.83 mmol) and 4-(6-(1-bromopropyl)pyridin-3-yl)benzonitrile (0.090 g) under nitrogen and the solution was heated to 70° C. for 3 h. After cooling the contents to rt, sodium bicarbonate was added, extracted with ethyl acetate (50 mL), the organic layer separated, the organic layer dried over sodium sulphate and distilled off to obtain the crude product. The compound was purified by preparative TLC using (2000μ; 5% MeOH/DCM) to provide 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)cyclohexa-1,3-dienecarbonitrile (0.012 g, 13.9% yield). 1H NMR (400 MHz DMSO-d6): δ 8.96 (d, 1H), 8.19 (dd, 1H), 7.96 (d, 5H); 7.47 (d, 1H), 7.39 (s, 1H), 7.01 (s, 1H), 5.45 (t, 1H), 2.26-2.23 (m, 2H), 0.84 (t, 3H): LC-MS m/z calcd for [M+H]+ 289.14. found 289.0.

Workup

temperatureAfter cooling the contents to rt
extractionextracted with ethyl acetate (50 mL)
customthe organic layer separated
dry with materialthe organic layer dried over sodium sulphate
distillationdistilled off
customto obtain the crude product
customThe compound was purified by preparative TLC

Sources & evidence

ORD record: ord-7c70993db4364863931762a2d6be8636
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199975B2

Reaction notes

Loading…