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Potassium Carbonate → N-(6-(1-oxoisoindolin-4-yl)naphthalen-2-yl)thiophene-3-carboxamide

HRID 908291
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 908291
Br[N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].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:3]1[C:4]2[C:9](=[C:8]([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:7]=[CH:6][CH:5]=2)[CH2:10][NH:2]1
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamideHCID 86611253Bromoisoindolin-1-one

Produkt 1

HCID 16035434N-(6-(1-oxoisoindolin-4-yl)naphthalen-2-yl)thiophene-3-carboxamideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Bromoisoindolin-1-one (11.5 mg, 0.0542 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (43.3 mg, 0.114 mmol), Fibercat palladium catalyst (Johnson-Matthey, 21.0 mg), and K2CO3 (2 M in water, 0.1 ml, 0.2 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (0.55 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) for 10 minutes at 50 Watts and 80 C. The reaction was cooled to room temperature, diluted with water (10 ml), and extracted with dichloromethane (6×5 ml). The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was washed with 15:1 hexanes/EtOAc and then purified on HPLC (10%->95% MeCN/water with 0.1% TFA) to afford title compound (4.9 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) for 10 minutes at 50 Watts and 80 C
  4. extractionextracted with dichloromethane (6×5 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe crude material was washed with 15:1 hexanes/EtOAc
  9. custompurified on HPLC (10%->95% MeCN/water with 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-64dc3422c39642ae86a3a05a0dfac1d7
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017601B2

Notizen zur Reaktion

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