Imidazole → 5-((1H-imidazol-1-yl)methyl)-2-bromopyridine

HRID 1054033Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>>[N:10]1([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

Reactant 4

HCID 795Imidazole

HCID 11430Potassium Carbonate

HCID 2855718-Crown-6

HCID 64246602-Bromo-5-bromomethylpyridine

Product 1

HCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Procedure

Synthesized using 1b (1.32 g, 5.26 mmol), imidazole (0.75 g, 11.00 mmol), K2CO3 (1.13 g, 8.16 mmol) and 18-crown-6 according to Method B. Yellow solid. Yield: 0.75 g, 60%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.12 (s, 2H), 6.88 (t, J=1.2 Hz, 1H), 7.13 (s, 1H), 7.28 (d, J=2.5 Hz, 1H), 7.48 (d, J=8.5 Hz, 1H), 7.56 (s, 1H), 8.28 (d, J=2.5 Hz, 1H); MS (ESI): m/z=239.08 [M+H]+.

Workup

customSynthesized

Sources & evidence

ORD record: ord-28b7cea98c2943a2aaab9fb62b343ea6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394290B2

Reaction notes

Loading…