2-Chloro-4-methoxypyridine → HCID 22473542, compound

HRID 2184044Notes

Reaction equation

HRID 2184044 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 19911282-Chloro-4-methoxypyridineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22473542HCID 22473542, compound

Procedure

2-Chloro-4-methoxypyridine (2.0 g, 13.9 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (4.75 g, 17.8 mmol) using the method in Example 47. Purification by chromatography on silica gel eluting with dichloromethane containing 20% isohexane then recrystallisation from toluene/isohexane gave 2-(2-fluoro-5-nitrophenyl)-4-methoxypyridine as a white solid: δH (400 MHz, CDCl3) 3.93 (3H, s), 6.88 (1H, dd, J 6 and 2), 7.31 (1H, t, J 10), 7.35-7.37 (1H, m), 8.24-8.29 (1H, m), 8.59 (1H, d, J 6), 8.98 (1H, dd, J 7 and 3).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 20% isohexane
  2. customrecrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-fe634fc18d724066a1c7b001a76137c1
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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