2-Chloro-6-methoxypyridine → HCID 22473546, compound

HRID 2184042Notes

Reaction equation

HRID 2184042 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[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]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1

Participants

3

Reactant 2

HCID 870092-Chloro-6-methoxypyridineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22473546HCID 22473546, compound

Procedure

2-Chloro-6-methoxypyridine (1.26 g, 8.81 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3 g, 11.45 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)-6-methoxypyridine as a white solid: δH (400 MHz, CDCl3) 4.05 (3H, s), 6.81 (1H, d, J 8), 7.30 (1H, dd, J 10 and 9), 7.48-7.51 (1H, m), 7.69 (1H, t, J 8), 8.22-8.26 (1H, m), 9.08 (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-06be1aaae66f46ac821d16c4b9740f88
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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