Water → tert-butyl 4-(4-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 522229

Reaktionsgleichung

Reaktionsgleichung von HRID 522229
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC=CC=3)(=O)=O)[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[OH-].[Na+].O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 690010591,1-dimethylethyl 4-[4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Produkt 1

HCID 118274390tert-butyl 4-(4-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of Example 135C (3.00 g, 5.63 mmol) and 20% sodium hydroxide in water (2.5 mL, 5.63 mmol) in dioxane (35 mL) was heated at 90° C. for 6 hours. The solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated to about 10 mL. The solid material was filtered, washed with ethyl acetate and dried to provide the title compound. MS (ESI+) m/z 378 (M+1).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to about 10 mL
  7. filtrationThe solid material was filtered
  8. washwashed with ethyl acetate
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f487124ff06c443f8af02adf241386ac
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328112B2

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