Cesium carbonate → Bms-911543

HRID 220390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220390
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH2:8])=[N:3]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:57]1([N:60]([CH:79]2[CH2:81][CH2:80]2)[C:61]([C:63]2[N:76]([CH2:77][CH3:78])[C:66]3=[N:67][C:68](I)=[C:69]4[N:73]=[CH:72][N:71]([CH3:74])[C:70]4=[C:65]3[CH:64]=2)=[O:62])[CH2:59][CH2:58]1>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:79]1([N:60]([CH:57]2[CH2:58][CH2:59]2)[C:61]([C:63]2[N:76]([CH2:77][CH3:78])[C:66]3=[N:67][C:68]([NH:8][C:4]4[CH:5]=[C:6]([CH3:7])[N:2]([CH3:1])[N:3]=4)=[C:69]4[N:73]=[CH:72][N:71]([CH3:74])[C:70]4=[C:65]3[CH:64]=2)=[O:62])[CH2:81][CH2:80]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70177471,5-dimethyl-1H-pyrazol-3-amineHCID 581806494-iodo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Produkt 1

HCID 50922691Bms-911543Ausbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a vial containing 1,5-dimethyl-1H-pyrazol-3-amine (13.60 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 μmol), Xantphos (5.90 mg, 10.20 μmol), and cesium carbonate (100 mg, 0.306 mmol) was added N,N-dicyclopropyl-6-ethyl-4-iodo-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (45.8 mg, 0.102 mmol) in DME (1020 μL). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 90° C. 1 h. The reaction mixture was diluted with dichloromethane and vacuum filtered through Celite. The filtrate was concentrated in vacuo. The crude residue was purified via flash column chromatography using an ISCO 12 g column eluting with 1-10% MeOH/CH2Cl2). N,N-Dicyclopropyl-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (14 mg, 31.7% yield) was isolated as an off-white solid.

Aufarbeitung

  1. customThe reaction mixture was sparged with argon for 5 min
  2. customthe vial was capped
  3. custom1 h
  4. additionThe reaction mixture was diluted with dichloromethane and vacuum
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe crude residue was purified via flash column chromatography
  8. washeluting with 1-10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-dfea846404ed4fea81b7bc61544c16f1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202881B2

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