Sodium Carbonate → HCID 25120563, Verbindung

HRID 1640927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640927
[F:1][C:2]1[C:3]([C:16]2[S:20][C:19]3[C:21](B4OC(C)(C)C(C)(C)O4)=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[N:12]2)=[N:6][CH:7]=1.[F:34][C:35]1C2[C:38](=[N:39][CH:40]=CC=2Br)[NH:37][CH:36]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl.[CH3:77][CH:78](O)[CH3:79]>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.CC#N.CS(C)=O.C1COCC1.O1CCOCC1.CN(C=O)C>[N:11]1([CH2:10][CH2:9][NH:8][C:5]2[N:4]=[C:3]([C:16]3[S:20][C:19]4[C:21]([C:77]5[C:35]([F:34])=[CH:36][N:37]=[C:38]6[NH:39][CH:40]=[CH:79][C:78]=56)=[CH:22][CH:23]=[CH:24][C:18]=4[CH:17]=3)[C:2]([F:1])=[CH:7][N:6]=2)[CH:15]=[CH:14][N:13]=[N:12]1

Komponenten

15

Edukt 7

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 17749109Barium hydroxide, octahydrateHCID 21906603Chloroform isopropyl alcoholHCID 66738069HCID 66738069, VerbindungHCID 667381024-Bromo-3-fluoro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 25120563HCID 25120563, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 7

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Combine {5-fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-yl}-(2-[1,2,3]triazol-1-yl-ethyl)-amine (0.105 g, 0.23 mmol), 3-fluoro-4-bromo-1H-pyrrolo[2,3-b]pyridine (51 mg, 0.30 mmol), barium hydroxide octahydrate (0.21 g, 0.68 mmol, alternatively sodium carbonate, potassium carbonate, sodium bicarbonate), Pd(dppf)Cl2 (20 mg, 0.025 mmol) in 2 mL of mixed solvent of DMF (alternatively dioxane, THF, DMSO, and CH3CN) and water (4/1, v/v). Heat the reaction mixture to 80° C. for 2.5 h. (or microwave heating for 10-60 min). Cool to RT. Dilute it with chloroform/IPA (3:1, v/v) 50 mL. Wash it 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 (0.05 g, 47%). MS (ES) m/z 475 [M+1]+.

Aufarbeitung

  1. temperature(or microwave heating for 10-60 min)
  2. temperatureCool to RT
  3. washWash it with water and saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. customRemove the organic solvent
  6. customto give the crude product
  7. customPurify by column chromatography (hexane to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c099a162d9de41d3a4ac2d3f8fcebe00
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114872B2

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