Potassium Phosphate, Tribasic → N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

HRID 2192176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192176
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=2[F:23])[N:4]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:3]=1.[CH:34]1(B(O)O)[CH2:36][CH2:35]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:34]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]3[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=3[F:23])[N:4]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:3]=2)[CH2:36][CH2:35]1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59741006N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

Produkt 1

HCID 59741001N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1.00 g (1.86 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide, 1.12 g (13.1 mmol) of cyclopropylboronic acid (Wallace, Debra J.; Chen, Cheng-yi; Tetrahedron Lett. 2002, 43(39), 6987-6990), 52.3 mg (0.19 mmol) of tricyclohexylphosphine and 1.39 g (6.53 mmol) of potassium phosphate are suspended in 10 ml of toluene and 0.5 ml of water. The solution is degassed, and 20.9 mg (0.09 mmol) of palladium(II) acetate are added. The mixture is heated at 100° C. for 1.5 h. After cooling, ethyl acetate is added and the organic phase is separated off and washed twice with water. The organic phase is dried over sodium sulfate and concentrated. The product is purified by preparative HPLC.

Aufarbeitung

  1. customThe solution is degassed
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. washwashed twice with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ef6747ea42574d43a07b33333ddc1c84
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329716B2

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