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

HRID 1036147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036147
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.[NH2:13][C:14]1[CH:19]=[N:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][N:15]=1.[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:17]3[N:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=3)=[CH:11][C:6]=2[CH:7]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 584873945-Bromo-2-fluoro-6-methyl-benzofuran

Produkt 1

HCID 584868455-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-pyrazine-2-ylamineAusbeute 25,4 %

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) (0.3 mmol), 2-aminopyrazine-5-boronic acid pinacol ester (133 mg, 2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (42 mg, 10% mol) and K3PO4 (127 mg, 0.6 mmol) in 1 ml ACN, 1 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 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)-pyrazine-2-ylamine (234) (18.5 mg, purity>95%, yield: 25.4%) 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-541fb0f297634d2fa69c4c1a09f6f33e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546403B2

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