Dimethylformamide → HCID 25120565, Verbindung

HRID 1640928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640928
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20](B5OC(C)(C)C(C)(C)O5)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Br[C:35]1[CH:40]=[CH:39][N:38]=[C:37]2[NH:41][CH:42]=[CH:43][C:36]=12.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].CN(C=O)C>C(Cl)(Cl)Cl.CC(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:35]5[CH:40]=[CH:39][N:38]=[C:37]6[NH:41][CH:42]=[CH:43][C:36]=56)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 17749109Barium hydroxide, octahydrateHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 66738069HCID 66738069, Verbindung

Produkt 1

HCID 25120565HCID 25120565, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Combine N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (0.28 g, 0.6 mmol), 4-bromo-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.51 mmol), barium hydroxide octahydrate (0.48 g, 1.52 mmol), Pd(dppf)Cl2 (40 mg, 0.05 mmol) in 4 mL of mixed solvent of DMF and water (4/1, v/v). Heat the reaction mixture to 80° C. for 45 min. Cool it to RT. Dilute with chloroform/IPA (3:1, v/v) 50 mL. Wash with water and saturated aqueous sodium chloride and dry over magnesium sulfate. Remove the organic solvent to give the crude product. Purify by column chromatography (hexane to ethyl acetate) to afford the title compound (0.17 g, 75%). MS (ES) m/z 457 [M+1]+.

Aufarbeitung

  1. temperatureCool it to RT
  2. washWash with water and saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. customRemove the organic solvent
  5. customto give the crude product
  6. customPurify by column chromatography (hexane to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3de2d4c64ee84fb188823c42b0cb19d7
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114872B2

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