Imidazole → 2-Bromo-3-imidazol-1-ylmethyl-pyridine

HRID 1054040Notes

Reaction equation

HRID 1054040 reaction equation
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[C:7]([CH2:8][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 109010782-Bromo-3-(bromomethyl)pyridine

Product 1

HCID 573298662-Bromo-3-imidazol-1-ylmethyl-pyridine

Procedure

Synthesized from 5a (891 mg, 2.78 mmol), imidazole (658 mg, 5.56 mmol) and K2CO3 (1.92 g, 13.9 mmol) according to Method B. Yield: 375 mg, 1.41 mmol, 51%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.23 (s, 2H), 6.96 (t, J=1.3 Hz, 1H), 7.07 (d, J=7.6 Hz, 1H) 7.15 (t, J=1.3 Hz, 1H), 7.24 (dd, J=7.6, 4.7 Hz, 1H), 7.66 (brs, 1H), 8.32 (dd, J=4.7, 1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=49.7, 119.3, 123.4, 130.0, 133.4, 136.6, 137.6, 142.0, 149.7; MS (ESI): m/z=239.10 [M+H]+.

Sources & evidence

ORD record
ord-519206a5b6a44ccfabbac36c1f33a857
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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