3-Ethoxyacryloyl chloride → (+/-)-(2E)-3-Ethoxy-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acrylamide

HRID 656837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656837
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[CH2:20]([O:22]/[CH:23]=[CH:24]/[C:25](Cl)=[O:26])[CH3:21]>ClCl.N1C=CC=CC=1>[CH2:20]([O:22]/[CH:23]=[CH:24]/[C:25]([NH:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2)=[O:26])[CH3:21]

Komponenten

5

Edukt 2

HCID 53255003-Ethoxyacryloyl chlorideHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Produkt 1

HCID 68675181(+/-)-(2E)-3-Ethoxy-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 24526ChlorineLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of (±)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (3.06 g, 12.2 mmol, described in Intermediate 4) in CH2 Cl2 (100 mL) and pyridine (40 mL) was added a solution of (E)-3-ethoxyacryloyl chloride [Tietze et al., Synthesis, 1993, 1079-1080](1.64 g, 12.2 mmol) in CH2 Cl2 (100 mL). The resulting mixture was stirred at ambient temperature for 1 h, then concentrated to dryness in vacuo. The residue was suspended in H2O (350 mL) with sonication and the solid was isolated by filtration and dried to give the title compound. MS: m/z=350 (M+1).

Aufarbeitung

  1. concentrationconcentrated to dryness in vacuo
  2. customThe residue was suspended in H2O (350 mL) with sonication
  3. customthe solid was isolated by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-59c4694491294a27827a2400ca5bdc9e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071772B2

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