Cesium carbonate → 2-(Isoquinolin-3-ylamino)-4-(4-tert-butoxycarbonylpiperazin-1-ylmethyl)-pyridine

HRID 1257124

Reaktionsgleichung

Reaktionsgleichung von HRID 1257124
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:22][C:23]1[N:24]=[CH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2.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)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOC(C)=O>[CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[C:23]([NH:22][C:17]2[CH:16]=[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]3)[CH:20]=[CH:19][N:18]=2)[N:24]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 311869Isoquinolin-3-AmineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866538601-Boc-4-(2-chloropyridin-4-ylmethyl)piperazine

Produkt 1

HCID 671756022-(Isoquinolin-3-ylamino)-4-(4-tert-butoxycarbonylpiperazin-1-ylmethyl)-pyridineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-Boc-4-(2-chloropyridin-4-ylmethyl)piperazine (500 mg, 1.63 mmol) (Preparation B-14) was mixed with 3-aminoisoquinoline (234 mg, 1.0 equiv), Pd2(dba)3 (148 mg, 0.1 equiv), xantphos (140 mg, 0.15 equiv), and Cs2CO3 (735 mg, 1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound (250 mg, yield 61%) was obtained as yellow solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. additionto dilute the mixture
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-66314b19fa0d4d94b2096323a4cd1b93
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461339B2

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