Sodium Hydroxide → 2-(3-methyl-1-m-tolylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515933
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:21]([CH3:23])[CH3:22])(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:22][CH:21]([CH3:23])[CH:20]=[C:19]([C:11]1[NH:10][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=1)[C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 672277341-benzenesulfonyl-2-(3-methyl-1-m-tolyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 672298562-(3-methyl-1-m-tolylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 1-benzenesulfonyl-2-(3-methyl-1-m-tolyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (2.99 g) in ethanol (50 mL) and tetrahydrofuran (100 mL) was treated with 10% aqueous sodium hydroxide solution (20 mL). The reaction was stirred at 85° C. for 14 h. The reaction mixture was cooled to 25° C. and concentrated in vacuo. Water (100 mL) was added to the residue, and the solution was extracted with ethyl acetate (2×100 mL). The organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. A light yellow solid was obtained and washed with ethanol (20 mL), then dried to afford 2-(3-methyl-1-m-tolylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.30 g, 77.8%) as a white solid: 1H NMR (300 MHz, CDCl3): δ ppm 9.50 (s, 1H), 7.98-7.89 (m, 2H), 7.23-7.01 (m, 5H), 6.50 (s, 1H), 5.64 (d, 1H, J=10.2 Hz), 2.98-2.90 (m, 1H), 2.32 (s, 3H), 1.12 (s, 3H), 1.10 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated in vacuo
  3. additionWater (100 mL) was added to the residue
  4. extractionthe solution was extracted with ethyl acetate (2×100 mL)
  5. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customA light yellow solid was obtained
  9. washwashed with ethanol (20 mL)
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-63c3ba0c73d04dccaa0515bd8ae90d82
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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