(4-Methoxyphenyl)boronic acid → 2,3-Dimethoxy-5-(4-methoxyphenyl)pyridine

HRID 1948255Notes

Reaction equation

HRID 1948255 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>>[CH3:9][O:8][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 125630845-Bromo-2,3-dimethoxypyridine

Product 1

HCID 693449082,3-Dimethoxy-5-(4-methoxyphenyl)pyridineYield 45%

Procedure

According to Scheme 4 Method B: The title compound was prepared from 5-bromo-2,3-dimethoxypyridine (1 eq, 1.83 mmol, 0.40 g) and 4-methoxyphenyl boronic acid (1 eq, 1.83 mmol, 0.28 g) according to the procedure described for Example 1 Step 3. The crude product was purified by flash chromatography on silica gel using cyclohexane/AcOEt 90/10 as eluent to afford the title compound 2,3-dimethoxy-5-(4-methoxyphenyl)pyridine (0.82 mmol, 0.20 g, 45%) was obtained.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bc21dbf75d2c42129fefe5f2de123103
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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