Potassium Carbonate → methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate

HRID 577540ノート

反応式

HRID 577540 の反応式
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.[CH:16]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[CH2:17].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:28]=[C:19]1[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:23])[N:18]1/[CH:16]=[CH:17]/[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 86723769Methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate

生成物 1

HCID 86723770methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate収率 34.3%

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a solution of methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate (112a, 3.40 g, 12.4 mmol) and N-vinylphthalimide (2.58 g, 14.9 mmol) in toluene (124 mL) was added K2CO3 (5.19 g, 37.2 mmol) followed by Pd(P(tBu)3)2 (0.400 g, 0.775 mmol). The reaction mixture was degassed and heated in a sealed tube at 110° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through CELITE®. H2O (100 mL) was added, the organic layer was separated and concentrated under vacuum, and the residue was purified by column chromatography (0-80%, ethyl acetate/heptanes) to give methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112b, 1.56 g, 34%) as yellow solid.

後処理

  1. customThe reaction mixture was degassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through CELITE®
  4. additionH2O (100 mL) was added
  5. customthe organic layer was separated
  6. concentrationconcentrated under vacuum
  7. customthe residue was purified by column chromatography (0-80%, ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-6a1c3afdff394f9980b3d6a1b061bff8
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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