Imidazole → HCID 71547907, compound

HRID 1497452Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of imidazole (0.0404 g, 0.595 mmol) in DMF (4 ml) was added potassium carbonate (0.123 g, 0.892 mmol) and 2-(1-bromoethyl)-5-(furan-3-yl)pyridine (0.075 g, 0.297 mmol) under nitrogen and the mixture was heated to 70° C. for 3 h. The contents were cooled to rt, sodium bicarbonate was added, the product extracted with ethyl acetate (100 ml), the organic layer was separated, the organic layer was dried over sodium sulphate and concentrated to obtain the crude product. The crude compound was purified by preparative TLC using (5% MeOH/DCM) to provide 2-(1-(1H-imidazol-1-yl)ethyl)-5-(furan-3-yl)pyridine as a yellow liquid (0.020 g, 28% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.81 (s, 1H), 8.25 (s, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 7.76 (s, 1H), 7.31 (s, 1H), 6.88 (d, 2H), 5.25 (t, 1H), 3.87 (s, 3H), 2.25-2.12 (m, 2H), 0.82 (t, 3H): LC-MS m/z calcd for [M+H]+ 240.11. found 240.4.

Workup

temperatureThe contents were cooled to rt
extractionthe product extracted with ethyl acetate (100 ml)
customthe organic layer was separated
dry with materialthe organic layer was dried over sodium sulphate
concentrationconcentrated
customto obtain the crude product
customThe crude compound was purified by preparative TLC

Sources & evidence

ORD record: ord-0ff4705aa7f847d790cca85a52282c93
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199975B2

Reaction notes

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