4-(1H-imidazol-1-yl)aniline → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine

HRID 1366165

Reaktionsgleichung

Reaktionsgleichung von HRID 1366165
OC1C=CC(CNC(=O)C2C=CC(NC3C4N(C=CN=4)C(C4C=NNC=4)=CN=3)=CC=2)=CC=1.[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37](Br)=[N:36][CH:35]=1.[N:44]1([C:49]2[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:48]=[CH:47][N:46]=[CH:45]1.CC([O-])(C)C.[Na+].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>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].C1(C)C=CC=CC=1>[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:55][C:52]2[CH:51]=[CH:50][C:49]([N:44]3[CH:48]=[CH:47][N:46]=[CH:45]3)=[CH:54][CH:53]=2)=[N:36][CH:35]=1

Komponenten

8

Edukt 5

HCID 3201654-(1H-imidazol-1-yl)anilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamideHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Produkt 1

HCID 59023113(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (203.8 mg, 0.736 mmol), 4-imidazol-1-yl-phenylamine (117.7 g, 0.739 mmol), NaOtBu (99 mg, 1.03 mmol), Pd2(dba)3 (27.0 mg, 0.0295 mmol), Xantphos (34.1 mg, 0.0589 mmol) and toluene (10 mL). The crude material is purified by Isolute FlashSilicaII cartridge chromatography eluting with 99:1 DCM:NH3 (7M in MeOH), followed by 97:3 DCM/NH3 (7M in MeOH). The title compound is isolated, after a second column chromatography purification using a 5:5:1 mixture EtOAc-petroleum ether-MeOH, as a yellow solid (104 mg, 40%).

Aufarbeitung

  1. customThe crude material is purified by Isolute FlashSilicaII cartridge chromatography
  2. washeluting with 99:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-06be650ada3544e78b5479809e709b82
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893058B2

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