Potassium Carbonate → N-(6-(2-oxoindolin-7-yl)naphthalen-2-yl)thiophene-3-carboxamide

HRID 908298

Reaktionsgleichung

Reaktionsgleichung von HRID 908298
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([NH:30][C:31]([C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)=[O:32])[CH:24]=[CH:23]3)O1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>[Pd].O>[O:11]=[C:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH:26]=[C:25]([NH:30][C:31]([C:33]3[CH:37]=[CH:36][S:35][CH:34]=3)=[O:32])[CH:24]=[CH:23]4)[CH:3]=[CH:4][CH:5]=2)[NH:9]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27732917-bromo-2,3-dihydro-1H-indol-2-oneHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide

Produkt 1

HCID 58828871N-(6-(2-oxoindolin-7-yl)naphthalen-2-yl)thiophene-3-carboxamideAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

7-bromoindolin-2-one (25.4 mg, 0.120 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (89.5 mg, 0.236 mmol), Fibercat palladium catalyst (Johnson-Matthey, 35.4 mg), and K2CO3 (2 M in water, 0.34 ml, 0.68 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.2 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C, first for 10 minutes, and then for 20 minutes. The reaction was cooled to room temperature, diluted with water (5 ml), and extracted with EtOAc (20 ml, 5 ml, 2×10 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on HPLC (10%->95% MeCN/water with 0.1% TFA). The fractions with product were purified on silica gel (3:2 hexanes/EtOAc->EtOAc->4:1 EtOAc/MeOH) to afford title compound (11.2 mg, 24%). MS (ESI pos. ion) m/z: 385 (M+H). Calc'd Exact Mass for C23H16N2O2S: 384.

Aufarbeitung

  1. additionwas added
  2. customThe reaction tube was sealed
  3. temperatureheated in the microwave (CEM microwave) at 60 Watts and 80 C, first for 10 minutes
  4. extractionextracted with EtOAc (20 ml, 5 ml, 2×10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on HPLC (10%->95% MeCN/water with 0.1% TFA)
  9. customThe fractions with product were purified on silica gel (3:2 hexanes/EtOAc->EtOAc->4:1 EtOAc/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-02dfc3aab4e6463586362cf7253977f5
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017601B2

Verknüpfte Notizen

Wird geladen…