Lithium Hydroxide → tert-butyl 2-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylcarbamoyl)morpholine-4-carboxylate

HRID 408320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408320
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][O:23][CH:22]([C:26](O)=[O:27])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.[Li+].[OH-]>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:26]([CH:22]3[O:23][CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:21]3)=[O:27])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Produkt 1

HCID 60205508tert-butyl 2-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylcarbamoyl)morpholine-4-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (350 mg, 1.52 mmol), 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (739 mg, 3.20 mmol), BOP-Cl (813 mg, 3.20 mmol), and triethylamine (1.06 mL, 7.61 mmol) in DCM (5 mL) was stirred at room temperature for 1 hour. 3M LiOH (3 mL) was then added, and stirred for an additional 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the solid formed was filtered. The solid product was washed with DCM (10 mL) and dried to give tert-butyl 2-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylcarbamoyl)morpholine-4-carboxylate (660 mg, 97.9% yield).

Aufarbeitung

  1. stirringstirred for an additional 10 minutes
  2. customthe solid formed
  3. filtrationwas filtered
  4. washThe solid product was washed with DCM (10 mL)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8c86943477614ba3b6c39f9f6cd228ca
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08758830B2

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