Sodium Carbonate → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-oxo-2,3-dihydro-1H-indol-6-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522400
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:43]=[C:42]3[C:38]([CH2:39][C:40](=[O:44])[NH:41]3)=[CH:37][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:35]2[CH:43]=[C:42]3[C:38]([CH2:39][C:40](=[O:44])[NH:41]3)=[CH:37][CH:36]=2)[CH:3]=1)=[O:15]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 467391626-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indol-2-oneHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Produkt 1

HCID 68078663N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-oxo-2,3-dihydro-1H-indol-6-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The title compound was prepared in the same manner as described in example 74 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-indol-2-one (63.1 mg, 0.243 mmol), DMSO(1.5 mL), sodium carbonate (0.281 mL, 0.562 mmol), and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 10 mg (11%). LCMS E-S (M+H)=471.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (d, J=6.8 Hz, 6 H), 2.13 (s, 3 H), 2.22 (s, 3 H), 3.58 (s, 2 H), 4.41 (d, J=4.8 Hz, 2 H), 5.31 (quin, J=6.6 Hz, 1 H), 5.91 (s, 1 H), 7.38 (d, J=7.6 Hz, 1 H), 7.73 (d, J=1.0 Hz, 1 H), 7.87 (dd, J=7.8, 1.5 Hz, 1 H), 8.12 (s, 1 H), 8.37 (s, 1 H), 9.00 (t, J=4.8 Hz, 1 H), 10.55 (s, 1 H), 11.58 (s, 1 H).

Aufarbeitung

  1. customThe final product was collected as 10 mg (11%)

Quellen und Nachweise

ORD-Eintrag
ord-c4425dfbb0df4b22a4c629706feae92a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073924B2

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