(4-Methoxyphenyl)boronic acid → HCID 69344963, compound

HRID 1948267Notes

Reaction equation

HRID 1948267 reaction equation
Br[C:2]1[C:3]([CH3:10])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[CH3:9][O:8][C:5]1[CH:4]=[C:3]([CH3:10])[C:2]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 41780025-Bromo-2-methoxy-4-methylpyridine

Product 1

HCID 69344963HCID 69344963, compoundYield 81%

Procedure

According to Scheme 30 Step 1: The title compound was prepared from 5-bromo-2-methoxy-4-methylpyridine (1 eq, 15.8 mmol, 3.20 g) and 4-methoxyphenylboronic acid (1.5 eq, 23.8 mmol, 3.61 g) according to the procedure described for Example 1 Step 3. Reaction conditions: 21 hours at 80° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 130 g SiO2) using AcOEt/MeOH (95/5) as the eluent to afford 2-methoxy-5-(4-methoxyphenyl)-4-methylpyridine (12.8 mmol, 2.94 g, 81%) as a light yellow solid.

Workup

  1. customReaction conditions
  2. custom21 hours
  3. customat 80° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 130 g SiO2)

Sources & evidence

ORD record
ord-0ec60736dbfe4fdca8e85f1ecbcb00d4
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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