3-Bromo-5-fluoropyridine → 3-Fluoro-5-(pyridin-4-yl)pyridine

HRID 878439Notes

Reaction equation

HRID 878439 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[N:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1>>[F:8][C:6]1[CH:7]=[C:2]([C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)[CH:3]=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 8202063-Bromo-5-fluoropyridineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 463158233-Fluoro-5-(pyridin-4-yl)pyridine

Procedure

Prepared from 3-bromo-5-fluoropyridine (439.0 mg, 2.50 mmol) and pyridin-4-ylboronic acid (509.9 mg, 3.73 mmol) according to Method K, except the product was purified by silica gel chromatography (ethyl acetate, Rf=0.21) instead of preparative HPLC: 1H NMR (300 MHz, chloroform-D) δ ppm 7.50-7.51 (m, 2H), 7.65 (dt, J=9.1, 2.4 Hz, 1H), 8.56 (d, J=2.8 Hz, 1H), 8.73-8.76 (m, 3H). MS (DCI/NH3) m/z=175 (M+H)+.

Workup

  1. customwas purified by silica gel chromatography (ethyl acetate, Rf=0.21) instead of preparative HPLC

Sources & evidence

ORD record
ord-d4d9c8eab83a4908af0cfc4594124300
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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