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Sodium borohydride → HCID 58009987, Verbindung

HRID 1628055
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1628055
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH:21]=[O:22])[N:20]=[C:15]2[CH:14]=1.[BH4-].[Na+]>O1CCOCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][OH:22])[N:20]=[C:15]2[CH:14]=1
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Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 58382343HCID 58382343, Verbindung

Produkt 1

HCID 58009987HCID 58009987, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (5.03 g, 11.5 mmol, prepared using D from Preparation #C.1. with (E)-styrylboronic acid and E) in 1,4-dioxane (65 mL) and EtOH (13 mL) was treated with NaBH4 (0.436 g, 11.5 mmol) then stirred overnight at rt. The reaction mixture was concentrated under reduced pressure then the residue was partitioned between EtOAc (125 mL) and saturated aqueous NaHCO3 (100 mL). The layers were separated then the aqueous layer was extracted with EtOAc (75 mL). The combined organic layers were extracted with brine (50 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on neutral alumina with 8:2 DCM/EtOAc then 7:3 DCM/EtOAc then finally EtOAc to give (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (3.19 g, 63%): LC/MS (Table 2, Method a) Rt=2.76 min; MS m/z 439 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc (125 mL) and saturated aqueous NaHCO3 (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (75 mL)
  5. extractionThe combined organic layers were extracted with brine (50 mL)
  6. dry with materialthen dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe material was purified by flash chromatography on neutral alumina with 8:2 DCM/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-76a0eee697fc4c2ab7630bad94597cbe
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785639B2

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