Cesium carbonate → 3-ethyl-1-phenyl-1H-indazol-6-amine

HRID 68693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68693
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH: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+].C1(C(C2C=CC=CC=2)=[NH:74])C=CC=CC=1>O1CCCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:17]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([NH2:74])=[CH:3][CH:4]=2)[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1)[CH3:18]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 674494686-bromo-3-ethyl-1-phenyl-1H-indazole

Produkt 1

HCID 674492303-ethyl-1-phenyl-1H-indazol-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-3-ethyl-1-phenyl-1H-indazole (300 mg, 1.00 mmol, 1.00 equiv) in tetrahydrofuran (30 mL), Xantphos (64 mg, 0.11 mmol, 0.11 equiv), Pd(OAc)2 (33 mg, 0.15 mmol, 0.15 equiv), Cs2CO3 (214 mg, 1.11 mmol, 1.11 equiv), diphenylmethanimine (200 mg, 1.10 mmol, 1.10 equiv). The resulting solution was heated to reflux for 16 h in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in tetrahydrofuran/3N hydrogen chloride (15 mL/5 mL). The resulting solution was stirred for an additional 2 h at room temperature, then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:MeOH:NH4OH (30:1:0.3) to yield 3-ethyl-1-phenyl-1H-indazol-6-amine as yellow oil.

Aufarbeitung

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 16 h in an oil bath
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. dissolutionThe residue was dissolved in tetrahydrofuran/3N hydrogen chloride (15 mL/5 mL)
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0be362da01f74ee180311003e9d2e7ed
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822447B2

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