HCID 178419772, Verbindung → HCID 178506201, Verbindung

HRID 42231

Reaktionsgleichung

Cl[C:2]1[N:3]=[N:4][C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[C:6]2[N:10]=[CH:9][NH:8][C:7]=12.[Br-].[CH2:28]([Zn+])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([C:2]1[N:3]=[N:4][C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[C:6]2[N:10]=[CH:9][NH:8][C:7]=12)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

7-Chloro-4-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-imidazo[4,5-d]pyridazine (149 mg, 0.389 mmol), benzyl zinc bromide (9.34 mL, 0.5M in THF, 4.67 mmol), and tetrakis (triphenylphosphine) palladium0 (23 mg, 0.020). The reaction mixture is heated to 80° C. for 32 h. Add H2O and extract product with EtOAc. Wash combined organics with brine and concentrate in vacuo. The residue is purified by flash chromatography on silica gel (60-100% EtOAc/Heptane flushed with 10% MeOH/EtOAc) to afford the title compound (12.1 mg, 7%).

Aufarbeitung

extractionAdd H2O and extract product with EtOAc
washWash
concentrationconcentrate in vacuo
customThe residue is purified by flash chromatography on silica gel (60-100% EtOAc/Heptane flushed with 10% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-a82b8d3137e643f49069a1098564f096
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536168B2

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