Triethylamine → HCID 66705970, Verbindung

HRID 1916175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916175
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[CH3:11][Si:12]([CH3:16])([CH3:15])[C:13]#[CH:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.C1CCCCC1.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>[CH2:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([C:14]#[C:13][Si:12]([CH3:16])([CH3:15])[CH3:11])=[CH:7][N:6]=1)[CH3:10]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 225049165-Bromo-N-ethylpyridin-2-amine

Produkt 1

HCID 66705970HCID 66705970, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The title compound is synthesized according to general procedure GP2 starting from 909 mg (4.5 mmol) 5-bromo-2-ethylamino-pyridine and 0.89 mL (6.3 mmol) 1-trimethylsilyl-ethyne using 26 mg (0.13 mmol) CuI, 118 mg (0.45 mmol) triphenylphosphine, 82 mg (0.12 mmol) PdCl2(PPh3)2 and 6.3 mL (45.0 mmol) triethylamine in 7 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient. Yield: 980 mg (99%).

Aufarbeitung

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-3f8ffb04704247aa80cb0f95fdb0b1ac
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618111B2

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