2,5-Dibromopyridine → Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate

HRID 49569

Reaktionsgleichung

Reaktionsgleichung von HRID 49569
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([NH:19][CH2:20][C:21]#[CH:22])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>C(NC(C)C)(C)C.C(OCC)(=O)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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:22]#[C:21][CH2:20][NH:19][C:9](=[O:10])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=1

Komponenten

7

Edukt 2

HCID 693532,5-DibromopyridineHCID 11137906Benzyl prop-2-yn-1-ylcarbamate

Produkt 1

HCID 21299382Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamateAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 7912DiisopropylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2,5-dibromopyridine (1.19 g), N-Cbz-propargylamine (1.04 g), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at ambient temperature for 3 hours under nitrogen. The mixture was diluted with ethyl acetate (50 mL). The mixture was filtered and washed with ethyl acetate (20 mL). The filtrate and wash were combined, concentrated under reduced pressure and triturated in MTBE to give crystalline 7-1 (1.28 g). The mother liquor was further purified by silica gel column chromatography using a mixture of MTBE: hexanes (1:1) to give an additional 280 mg of 7-1.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate (20 mL)
  3. washThe filtrate and wash
  4. concentrationconcentrated under reduced pressure
  5. customtriturated in MTBE

Quellen und Nachweise

ORD-Eintrag
ord-26c2d7fafdc044be956e21bc0a6f0e9f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706885B2

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