Imidazole → 2-Bromo-5-(2-iodoethyl)pyridine

HRID 533524Notes

Reaction equation

HRID 533524 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:35]I>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][I:35])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 224732202-(6-Bromopyridin-3-yl)ethanol

Product 1

HCID 866687632-Bromo-5-(2-iodoethyl)pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(6-bromopyridin-3-yl)ethanol (2.0 g, 9.9 mmol, 1.0 equiv) in dichloromethane (31 mL) was added dropwise to a solution of imidazole (0.91 g, 13.4 mmol, 1.4 equiv), triphenylphosphine (3.3 g, 12.4 mmol, 1.3 equiv), and iodine (3.1 g, 12.4 mmol, 1.3 equiv) in dichloromethane (31 mL) at room temperature. After stirring for 6 h, the reaction was filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (15% ethyl acetate in heptane) to provide the title compound as a white solid (2.83 g, 92%). MS (LCMS) m/z 312.0 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.15 (t, J=7.03 Hz, 2H) 3.43 (t, J=7.03 Hz, 2H) 7.54 (d, J=7.81 Hz, 1H) 7.61 (dd, J=8.20, 2.73 Hz, 1H) 8.22 (d, J=2.34 Hz, 1H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica gel (15% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-59a8a528fdfa441499136410836e4152
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

Loading…