2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic Acid → 2-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetic acid

HRID 1948220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948220
[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.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=2)O1>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:8](=[O:14])[CH:9]=[CH:10][C:11]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=3)=[CH:12]2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic AcidHCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one

Produkt 1

HCID 694404232-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetic acidAusbeute 101,2 %

Versuchsvorschrift

According to Scheme 3 Method A: The title compound was prepared according to Example 2 Step 2, from 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 0.67 mmol, 0.20 g, Example 2 Step 1) and 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (1.5 eq, 1.00 mmol, 0.26 g). Reaction conditions: 4.5 hours at 90° C. The reaction mixture was made acidic then extracted with AcOEt. The organic layer washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography over silicagel (AIT Flashsmart prepacked column 25 g SiO2, AcOEt/MeOH 95/5), yielding the title compound (0.24 g, 100%) as a white solid. LC (XTerra RP18, 3.5 μm, 3.0×50 mm Column): RT=3.53 min; MS m/z (CI) [MH]+=354, 356.

Aufarbeitung

  1. customThe title compound was prepared
  2. customReaction conditions
  3. custom4.5 hours
  4. customat 90° C
  5. extractionThe reaction mixture was made acidic then extracted with AcOEt
  6. washThe organic layer washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography over silicagel (AIT Flashsmart prepacked column 25 g SiO2, AcOEt/MeOH 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-83d7182346944f4181468ec22a3e45ab
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399493B2

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