4-Methylmorpholine → 5-Bromo-2-(pyrrolidine-1-carbonyl)-1H-indole

HRID 591683

Reaktionsgleichung

Reaktionsgleichung von HRID 591683
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.C(N=C=N[CH2:20][CH2:21][CH2:22][N:23]([CH3:25])C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.N1CCCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:23]1[CH2:22][CH2:21][CH2:20][CH2:25]1)=[O:13])=[CH:5]2

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 2521375-Bromo-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 471546575-Bromo-2-(pyrrolidine-1-carbonyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 5-bromo-1H-indole-2-carboxylic acid (1.0 g, 4.2 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) (1.1 g, 5.9 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (0.62 g, 4.6 mmol) in THF (20 mL) was added 4-methylmorpholine (NMM) (0.65 mL, 5.9 mmol). After 10 minutes, pyrrolidine (0.73 mL, 8.8 mmol) was added. The mixture was stirred at room temperature under nitrogen for 17 hours. The solvent was removed under reduced pressure. Water was added, stirred for 0.5 hours. The solid was filtered, washed with water, and dried in air to afford (5-bromo-1H-indol-2-yl)-pyrrolidin-1-yl-methanone as a pale yellow solid. Yield: 1.2 g (95%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionWater was added
  3. stirringstirred for 0.5 hours
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried in air

Quellen und Nachweise

ORD-Eintrag
ord-9ca0f7c273b54587bb502bf8a4bb6f49
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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