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Potassium Carbonate → 1-(4-{4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzyl}-piperazin-yl)-ethanone

HRID 712565
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 712565
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=1.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].C([O-])([O-])=O.[K+].[K+].Br[C:34]1[CH:35]=[C:36]2[C:42]([C:43]3[CH:44]=[C:45]4[C:49](=[CH:50][CH:51]=3)[NH:48][CH:47]=[CH:46]4)=[CH:41][N:40](S(C3C=CC(C)=CC=3)(=O)=O)[C:37]2=[N:38][CH:39]=1>CN(C=O)C.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>[NH:48]1[C:49]2[C:45](=[CH:44][C:43]([C:42]3[C:36]4[C:37](=[N:38][CH:39]=[C:34]([C:6]5[CH:5]=[CH:4][C:3]([CH2:2][N:24]6[CH2:25][CH2:26][N:21]([C:18](=[O:20])[CH3:19])[CH2:22][CH2:23]6)=[CH:8][CH:7]=5)[CH:35]=4)[NH:40][CH:41]=3)=[CH:51][CH:50]=2)[CH:46]=[CH:47]1
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 837951-AcetylpiperazineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 462360471-(4-{4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzyl}-piperazin-yl)-ethanone
Ausbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (100 mg, 0.337 mmol), N-acetylpiperazine (47 mg, 0.37 mmol) and K2CO3 (93 mg, 0.675 mmol) were combined in DMF (2.5 ml) and stirred overnight at room temperature. The reaction was quenched by the addition of water, extracted with DCM and dried. The residue was taken up in CH3CN (2 ml), Intermediate B (120 mg, 0.275 mmol) and dichlorobis(triphenylphosphine)palladium (II) (10 mg, 0.013 mmol) were added and the reaction was heated to 150° C. in a microwave reactor for 20 min. The mixture was partitioned between water and DCM, the organic phase dried, evaporated and purified by silica gel chromatography using 0-5% MeOH:DCM. 53 mg (46%) of the title compound were obtained. MS ESI (m/z): 450.4 (M+1)+, calc. 449.

Aufarbeitung

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with DCM
  3. customdried
  4. temperaturethe reaction was heated to 150° C. in a microwave reactor for 20 min
  5. customThe mixture was partitioned between water and DCM
  6. customthe organic phase dried
  7. customevaporated
  8. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9db4a4f21d5f4c088dd7c7789903fbd3
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181247B2

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