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Potassium Phosphate, Tribasic → N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

HRID 1467340
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467340
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][CH:14]3[CH2:19][CH:18]([CH2:20][C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=4[F:28])[CH2:17][N:16]([CH3:29])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:57][C:58]1[CH:63]=[C:62](B2OC(C)(C)C(C)(C)O2)[CH:61]=[CH:60][N:59]=1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([F:28])[C:21]=1[CH2:20][CH:18]1[CH2:17][N:16]([CH3:29])[CH2:15][CH:14]([NH:13][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:3]=[C:2]3[C:62]2[CH:61]=[CH:60][N:59]=[C:58]([CH3:57])[CH:63]=2)=[O:12])[CH2:19]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 679965083-bromo-N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-1-trityl-1H-indazole-5-carboxamide

Produkt 1

HCID 70653003N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-bromo-N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-1-trityl-1H-indazole-5-carboxamide (0.050 g, 0.0716 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (0.0052 g, 0.00716 mmol), Potassium phosphate tribasic (0.046 g, 0.215 mmol) and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.018 g, 0.0788 mmol) was added into a flask. After purging the reaction vessel with nitrogen gas, dioxane (0.215 mL) and water (0.043 mL) was added. The reaction was allowed to stir at 80° C. for 16 hrs. The reaction was quenched with water (1 mL) and extracted with dichloromethane (3×1 mL). The extracts were combined, dried using sodium sulfate, filtered through celite, and concentrated under vacuo. The crude product was progressed to the next step without further purification. LC-MS found 718.2, calcd M+H 718.3.

Aufarbeitung

  1. customAfter purging the reaction vessel with nitrogen gas, dioxane (0.215 mL) and water (0.043 mL)
  2. additionwas added
  3. customThe reaction was quenched with water (1 mL)
  4. extractionextracted with dichloromethane (3×1 mL)
  5. customdried
  6. filtrationfiltered through celite
  7. concentrationconcentrated under vacuo
  8. customThe crude product was progressed to the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a22383aa91e64f4583b726ecf591ef8f
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999957B2

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