Sodium hydride → (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one

HRID 1854397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854397
[CH:1]1([C:7](=[O:17])[CH2:8]P(=O)(OCC)OCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[S:20]([N:30]1[C:34]2=[N:35][CH:36]=[C:37]([CH:39]=O)[N:38]=[C:33]2[CH:32]=[CH:31]1)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH:1]1([C:7](=[O:17])/[CH:8]=[CH:39]/[C:37]2[N:38]=[C:33]3[CH:32]=[CH:31][N:30]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[C:34]3=[N:35][CH:36]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11043558Diethyl (2-cyclohexyl-2-oxoethyl)phosphonateHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

Produkt 1

HCID 58010004(E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-oneAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of diethyl 2-cyclohexyl-2-oxoethylphosphonate (0.609 g, 2.32 mmol) in THF (10 mL) was added NaH (60% dispersion in mineral oil, 0.0664 g, 1.66 mmol). After about 30 min, a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (0.20 g, 0.64 mmol, Example #10, Step B) in THF (10 mL) was added. After about 2 h, EtOAc (50 mL) and saturated aqueous NH4Cl (50 mL) was added to the reaction mixture. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with IPA (20 mL) to provide (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one as a tan solid (0.20 g, 73%): LC/MS (Table 2, Method a) Rt=3.06 min; MS m/z: 410 (M+H)+.

Aufarbeitung

  1. waitAfter about 2 h
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with IPA (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-38a886072d5d457a94d549f261d0455f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962629B2

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