Ethyl Acetate → Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate

HRID 49571

Reaktionsgleichung

Reaktionsgleichung von HRID 49571
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([NH:16][CH2:17][C:18]#[CH:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[C:20]([NH:30][CH2:31][C:32]#[CH:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(OCC)(=O)C>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:12]([O:11][C:9]([NH:16][CH2:17][C:18]#[C:19][C:2]1[N:3]=[CH:4][C:5]([C:33]#[C:32][CH2:31][NH:30][C:20](=[O:21])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][CH:7]=1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 693532,5-DibromopyridineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 11137906Benzyl prop-2-yn-1-ylcarbamate

Produkt 1

HCID 21299383Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamateAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 7912DiisopropylamineLösungsmittel

Versuchsvorschrift

A mixture of 2,5-dibromopyridine (1.19 g), N-Boc-propargylamine (781 mg), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at room temperature overnight under nitrogen atmosphere. To the mixture was added N-Cbz-propargylamine (1.14 g) and the mixture was heated under reflux temperature for 5 hours under nitrogen atmosphere. The mixture was cooled to room temperature. To the mixture was added ethyl acetate (50 mL). The precipitates were filtered and washed with ethyl acetate. The filtrate and washings were combined and purified by silica gel column to give 6-1 (250 mg) as a crystalline compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux temperature for 5 hours under nitrogen atmosphere
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe precipitates were filtered
  5. washwashed with ethyl acetate
  6. custompurified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-23e7eb85123f438d84ad90e4f736190c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706885B2

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