Dichloromethane → US9156811, Ddd86206

HRID 1749366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749366
C[N:2]([C:20]1[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=1[CH3:25])[S:3]([C:6]1[CH:11]=[CH:10][C:9](C2C=CC=C(C=O)C=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[N:28]1([C:34]2[CH:39]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:37]=[CH:36][N:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)[Cl:58]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:58][C:11]1[CH:10]=[C:9]([C:38]2[CH:37]=[CH:36][N:35]=[C:34]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:39]=2)[CH:8]=[CH:7][C:6]=1[S:3]([NH:2][C:20]1[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=1[CH3:25])(=[O:4])=[O:5]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 162179482-(1-Piperaziny) pyridine-4-boronic acid pinacol esterHCID 907170953'-Formyl-biphenyl-4-sulfonic acid methyl-(1,3,5-trimethyl-1h-pyrazol-4-yl)-amide

Produkt 1

HCID 46179031US9156811, Ddd86206Ausbeute 1.483,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Prepared from the sulphonamide of intermediate 3 (500 mg, 1.3 mmol), 2-(1-piperazinyl)pyridine-4-boronic acid pinacol ester (580 mg, 2.0 mmol), tribasic potassium phosphate (427 mg, 2.0 mmol), and Pd(dppf)Cl2.DCM (50 mg, 0.06 mmol) in DMF (3.0 ml) and water (0.75 ml), according to the method of intermediate 11, to give the title compound as an off-white powder (412 mg, 0.89 mmol, 68%). δH (D-6 DMSO, 300K) 8.20 (1H, d J 5.2 Hz), 8.14 (1H, d J 1.7 Hz), 7.84 (1H, dd J 1.75 Hz 8.3 Hz), 7.79 (1H, d J 8.3 Hz), 7.13 (1H, s), 6.99 (1H, dd J 1.15 Hz 5.2 Hz), 3.55 (3H, s), 3.51 (4H, s br), 2.79 (4H, s br), 1.90 (3H, s), 1.69 (3H, s). m/z (ES+, 70V) 461.2 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-ec606811be354cb7b0843fad1267b6c3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156811B2

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