Trimethylsilylacetylene → 2-(5-Ethynylisochroman-1-yl)-4,5-dihydro-1H-imidazole

HRID 1771415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771415
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.[C:17]([Si](C)(C)C)#[CH:18]>CCN(CC)CC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:17]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)#[CH:18]

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 717669082-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole

Produkt 1

HCID 717672062-(5-Ethynylisochroman-1-yl)-4,5-dihydro-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a degassed solution of 2-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole (300 mg) in Et3N (10 ml) and ethynyltrimethylsilane (210 mg) was added tetrakis(triphenylphosphine)-palladium (37 mg). The mixture was degassed with N2 and heated in a microwave oven for 60 min at 120° C. The reaction mixture was concentrated under vacuum and purified by separation method K. K2CO3 was added to the reaction crude (in MeOH) and the mixture was stirred 4 h at it. The title compound was isolated by a separation method G. (Yield 6.2 mg).

Aufarbeitung

  1. customThe mixture was degassed with N2
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. custompurified by separation method K
  4. additionK2CO3 was added to the reaction crude (in MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-5de70b8108b442bf833bba75367ebcb6
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249127B2

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