Cesium carbonate → HCID 71061452, Verbindung

HRID 875372

Reaktionsgleichung

Reaktionsgleichung von HRID 875372
Br[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:17]1([C:21]([NH2:23])=[O:22])[CH2:20][CH2:19]C1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[NH:8]1[C:7]2=[C:2]([NH:23][C:21]([CH:17]3[CH2:20][CH2:19]3)=[O:22])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 1274476Cyclobutanecarboxamide2×HCID 196964567-Bromo-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 71061452HCID 71061452, VerbindungAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 7-bromo-1H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone) dipalladium (116.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4). The resulting reaction mixture was heated to 120° C. and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropane carboxamide (200 mg, 36% yield).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel (100-200) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-565884b6943b4f10915d60089e539388
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980911B2

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