Dichloromethane → 2,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

HRID 2234670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234670
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=3)=[CH:9][N:8]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[NH2:26][C:27]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:28]=1[C:29]([N:31]([CH3:33])[CH3:32])=[O:30].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(#N)C>[NH2:26][C:27]1[CH:37]=[CH:36][C:35]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=4)=[CH:9][N:8]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]3=[N:6][CH:7]=2)=[CH:34][C:28]=1[C:29](=[O:30])[N:31]([CH3:32])[CH3:33]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 574162382-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 577314872,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Produkt 1

HCID 577315452,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester, 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide, [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) complex with dichloromethane, acetonitrile, 1M aqueous sodium carbonate solution, and tetrahydrofuran were combined in a microwave vial. The tube was placed in a microwave reactor and irradiated to 120° C. for 20 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes) to give 2,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 489.3 (M+H+).

Aufarbeitung

  1. customThe tube was placed in a microwave reactor
  2. customirradiated to 120° C. for 20 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-63f2728b39f64a5d96dcce30a8a8832e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709645B2

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