1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenyl]amine

HRID 1366151

Reaktionsgleichung

Reaktionsgleichung von HRID 1366151
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[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:50]1[N:51]=[N:52][N:53]([C:55]2[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=2)[CH:54]=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:61][C:58]2[CH:59]=[CH:60][C:55]([N:53]3[CH:54]=[C:50]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=4)[N:51]=[N:52]3)=[CH:56][CH:57]=2)=[N:36][CH:35]=1

Komponenten

8

Edukt 5

HCID 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]pyrazineHCID 590231334-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine

Produkt 1

HCID 59023107(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-pyridin-2-yl-[1,2,3]triazol-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 (80.5 mg, 0.291 mmol), 4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine (68.3 g, 0.288 mmol), NaOtBu (38.2 mg, 0.403 mmol), Pd2(dba)3 (10.5 mg, 0.0115 mmol), Xantphos (13.3 mg, 0.023mmol) and toluene (4 mL). The crude material is purified by silica gel column chromatography eluting with 98:2 DCM:MeOH followed by 97:3 DCM:MeOH affording the title compound (52.8 mg, 42%).

Aufarbeitung

  1. customThe crude material is purified by silica gel column chromatography
  2. washeluting with 98:2 DCM

Quellen und Nachweise

ORD-Eintrag
ord-cf5af2bf34b34aa8992337fb51c4d67b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893058B2

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