Potassium Carbonate → HCID 178477698, Verbindung

HRID 1888252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888252
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH2:15][CH2:14]1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[F:31].C(=O)([O-])[O-:36].[K+].[K+]>O1CCOCC1.O>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:12])=[O:36])[CH:10]=2)[NH:7][N:6]=[C:5]3[CH:13]2[CH2:14][CH2:15][N:16]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH2:17][CH2:18]2)[CH:28]=[CH:29][C:30]=1[F:31]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 178477688HCID 178477688, Verbindung2×

Produkt 1

HCID 178477698HCID 178477698, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

Following the general procedure of Example 66, a mixture of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indazole-7-carbonitrile (Intermediate 10) (50 mg, 0.102 mmols), 3,4-difluorophenyl boronic acid (48 mg, 0.306 mmols), potassium carbonate (84 mg, 0.612 mmol), and chloro(di-2-norbonylphosphino)-(2-dimethylaminomethyl-ferrocen-1-yl)paladium (3 mg) in dioxane/water (3/1, 4 mL) was reacted. The reaction mixture was concentrated, redissolved in methylene chloride and filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (11 mg, 24%)

Aufarbeitung

  1. customwas reacted
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionredissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified
  7. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-954482f1b59d4f86b19fa73a127b4ec9
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501780B2

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