4-(Hydroxymethyl)benzeneboronic acid → HCID 69349174, compound

HRID 1948245Notes

Reaction equation

HRID 1948245 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[OH:17][CH2:18][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]([CH2:18][OH:17])=[CH:20][CH:21]=3)[CH:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one

Product 1

HCID 69349174HCID 69349174, compoundYield 52.1%

Procedure

According to Scheme 25 Step 2: The title compound was prepared from 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 3.30 mmol, 1.00 g, Example 2 Step 1) and 4-(hydroxymethyl)phenylboronic acid (1.5 eq, 5.00 mmol, 0.76 g) according to the procedure described for Example 1 Step 3. Reaction conditions: overnight at 80° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2) using CH2Cl2/MeOH 98/2 as the eluent to afford 1-(4-chlorobenzyl)-5-(4-(hydroxymethyl)phenyl)pyridin-2(1H)-one (1.72 mmol, 0.62 g, 52%) as a brown oil LC (XTerra RP18, 3.5 μm, 3.0×50 mm Column): RT=3.47 min; MS m/z (CI) [MH]+=326, 328.

Workup

  1. customReaction conditions
  2. customovernight
  3. customat 80° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2)

Sources & evidence

ORD record
ord-d41f30687bd44759b72ce91e326f7a7d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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