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Cesium carbonate → 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

HRID 716030
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 716030
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[OH:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]3=[N:6][CH:7]=2)=[CH:27][CH:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 693314-Aminobenzyl alcoholHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

Produkt 1

HCID 710153161-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneAusbeute 215,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator
HCID 634876Binap, (A+-)-Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a 35 ml sealed tube, 1-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one (2.0 g, 0.0048 mole) and (4-aminophenyl)methanol (0.78 g, 0.0063 mole) was taken in toluene (20.0 ml). The reaction mixture was purged with argon for 15 min at RT followed by Cs2CO3 (4.7 g, 0.0144 mole) was added and further purged for 30 min with argon. BINAP (0.06 g, 0.0001 mole) and Pd(OAc)2 (0.021 g, 0.0001 mole) were added to reaction mixture and heated to 110° C. for 4 hr. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with ethyl acetate. Filtrate was collected and concentrated to afford crude product which was subjected for the column purification. The reaction with repeated twice and the crude product from each reaction was mixed and then purified using column purification by eluting the compound with 25-30% ethyl acetate in hexanes to yield 4.7 g of 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one.

Aufarbeitung

  1. customTo a 35 ml sealed tube
  2. customThe reaction mixture was purged with argon for 15 min at RT
  3. additionwas added
  4. customfurther purged for 30 min with argon
  5. customAfter completion of the reaction
  6. filtrationthe reaction mixture was filtered through celite bed
  7. washwashed with ethyl acetate
  8. customFiltrate was collected
  9. concentrationconcentrated
  10. customto afford crude product which
  11. customwas subjected for the column purification
  12. customThe reaction
  13. custompurified
  14. customcolumn purification
  15. washby eluting the compound with 25-30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-44c5969376e24a048035e85f1ceb0000
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187487B2

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