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 577540노트

반응식

HRID 577540 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a1c3afdff394f9980b3d6a1b061bff8
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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