Potassium Carbonate → (R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamate

HRID 79538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79538
Br[C:2]1[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:35])[C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[C:17](=[O:35])[N:14]2[CH2:15][CH2:16][N:11]([C:3]3[C:2]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:7][N:6]=[C:5]4[NH:8][CH:9]=[CH:10][C:4]=34)[CH2:12][CH2:13]2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 68763825(R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 68761687(R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.180 g, 0.320 mmol, see Example 1), phenylboronic acid (0.0468 g, 0.384 mmol), Pd(PPh3)4 (0.0185 g, 0.0160 mmol) and 10% K2CO3 (aq., 0.66 mL, 0.47 mmol) were added to an Ar degassed solution of 2:1 toluene:EtOH (3 mL). The reaction was then heated to 80° C. overnight. The reaction was then cooled to room temperature, diluted with water, and extracted with DCM. The organic fractions were dried, filtered, concentrated, and purified (500:10-500:15) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamate (0.018 g, 10.0% yield).

Aufarbeitung

  1. customdegassed solution of 2:1 toluene
  2. temperatureThe reaction was then cooled to room temperature
  3. additiondiluted with water
  4. extractionextracted with DCM
  5. customThe organic fractions were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified (500:10-500:15)

Quellen und Nachweise

ORD-Eintrag
ord-4c862b85839c402c9f84e0afe6424c93
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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