Ethyl Acetate → 5-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine

HRID 874672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874672
Br[C:2]1[C:3]([CH3:12])=[CH:4][C:5]2[O:9][C:8]([F:10])=[CH:7][C:6]=2[CH:11]=1.FC1(F)OC2C=C(C)C(C3N=C[C:26]([NH:29][C:30](=O)[C:31]4[CH:36]=[CH:35]C=CC=4F)=[N:27]C=3)=CC=2O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O>[F:10][C:8]1[O:9][C:5]2[CH:4]=[C:3]([CH3:12])[C:2]([C:31]3[CH:36]=[CH:35][C:26]([NH2:27])=[N:29][CH:30]=3)=[CH:11][C:6]=2[CH:7]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamideHCID 584873945-Bromo-2-fluoro-6-methyl-benzofuran

Produkt 1

HCID 584874145-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamineAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 5-bromo-2-fluoro-6-methyl-benzofuran (230) (78.5 mg, 0.34 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (151 mg, 2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (48 mg, 10% mol) and K3PO4 (145 mg, 0.69 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 3 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine (231) (46.8 mg, purity>95%, yield: 56.8%) as yellow solid.

Aufarbeitung

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0eeec9aa0885469db772443ea71ccafd
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980629B2

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