Potassium Carbonate → N-(6-(2-amino-3-carbamoyl-5-methylphenyl)naphthalen-2-yl)thiophene-3-carboxamide

HRID 908309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908309
[NH2:1][C:2]1[C:10](Br)=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([NH:31][C:32]([C:34]2[CH:38]=[CH:37][S:36][CH:35]=2)=[O:33])[CH:25]=[CH:24]3)O1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>[Pd].O>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[NH2:6])=[CH:7][C:8]([CH3:12])=[CH:9][C:10]=1[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([NH:31][C:32]([C:34]1[CH:38]=[CH:37][S:36][CH:35]=1)=[O:33])[CH:25]=[CH:24]2

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 588288742-Amino-3-bromo-5-methylbenzamideHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide

Produkt 1

HCID 58828862N-(6-(2-amino-3-carbamoyl-5-methylphenyl)naphthalen-2-yl)thiophene-3-carboxamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-amino-3-bromo-5-methylbenzamide (31.8 mg, 0.139 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (122 mg, 0.370 mmol), Fibercat palladium catalyst (Johnson-Matthey, 68.2 mg), and K2CO3 (2 M in water, 0.51 ml, 1.0 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.5 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C for 20 minutes. The reaction was then cooled to room temperature, diluted with water (5 ml), and extracted with EtOAc (4×10 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified via silica gel (Biotage instrument, 13%->50%->100% EtOAc/hexanes) to afford title compound (5.6 mg, 10%). MS (ESI pos. ion) m/z: 402 (M+H). Calc'd Exact Mass for C23H19N3O2S: 401.

Aufarbeitung

  1. additionwas added
  2. customThe reaction tube was sealed
  3. temperatureheated in the microwave (CEM microwave) at 60 Watts and 80 C for 20 minutes
  4. extractionextracted with EtOAc (4×10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via silica gel (Biotage instrument, 13%->50%->100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1b4f42a32f1445e5861fea74e4768f8c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017601B2

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