(4-Methoxyphenyl)boronic acid → HCID 58966963, compound

HRID 1948251Notes

Reaction equation

HRID 1948251 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[N:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[N:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 69350494HCID 69350494, compound

Product 1

HCID 58966963HCID 58966963, compoundYield 71%

Procedure

According to Scheme 27 Step 2: The title compound was prepared from 1-(4-chlorobenzyl)-5-bromopyrazin-2(1H)-one (1 eq, 0.67 mmol, 0.20 g) and 4-methoxyphenylboronic acid (1.5 eq, 1.00 mmol, 0.15 g) according to the procedure described for Example 1 Step 3. Reaction conditions: 1 hour at 80° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/MeOH (98/2) as the eluent to afford 1-(4-chlorobenzyl)-5-(4-methoxyphenyl)pyrazin-2(1H)-one (0.47 mmol, 0.15 g, 71%) as a beige solid.

Workup

  1. customReaction conditions
  2. custom1 hour
  3. customat 80° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-46e9773313ee43f9a71595038138c77f
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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