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 1948220노트

반응식

HRID 1948220 반응식
[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

참가 물질

3

반응물 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

생성물 1

HCID 694404232-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetic acid수율 101.2%

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-83d7182346944f4181468ec22a3e45ab
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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