Imidazole → 3-Bromo-2-chloro-5-imidazol-1-ylmethyl-pyridine

HRID 1054042Notes

Reaction equation

HRID 1054042 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[C:6]([CH2:8][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 848198723-Bromo-5-(bromomethyl)-2-chloropyridine

Product 1

HCID 706831103-Bromo-2-chloro-5-imidazol-1-ylmethyl-pyridine

Procedure

Synthesized from 6a (2.38 g, 8.34 mmol), imidazole (1.14 g, 16.7 mmol) and K2CO3 (5.76 g, 41.7 mmol) according to Method B. Yield: 1.88 g, 6.90 mmol, 83%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.14 (s, 2H), 6.89 (bs, 1H), 7.13 (d, J=4.0 Hz, 1H), 7.61-7.63 (m, 1H), 7.70 (brs, 1H), 8.20 (brs, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=46.8, 118.9, 120.8, 130.5, 132.2, 137.2, 140.8, 146.3, 150.9; MS (ESI): m/z=272.05 [M+H]+.

Sources & evidence

ORD record
ord-5eb616b4e1324240a8c10d282e82e3f7
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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