Water → 6-(Spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)-3-pyridinamine

HRID 1023633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023633
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[C:16]3[C:17]4([CH2:20][O:21][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH2:19][CH2:18]4)=[N:8][CH:9]=1)([O-])=O.O.[Cl-].[NH4+]>O1CCCC1>[C:17]12([C:16]3[C:11]([O:10][C:7]4[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=4)=[CH:12][CH:13]=[CH:14][C:15]=3[O:21][CH2:20]1)[CH2:19][CH2:18]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 672364775-Nitro-2-(spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)pyridine2×

Produkt 1

HCID 672354596-(Spiro[1-benzofuran-3,1'-cyclopropan]-4-yloxy)-3-pyridinamineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-nitro-2-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)pyridine (Reference Intermediate 215, 99 mg) in tetrahydrofuran (5 ml)/water (2.5 ml) iron (97 mg, 1.741 mmol) and then ammonium chloride (93 mg, 1.741 mmol) were added and the reaction mixture was stirred for 4 hours at room temperature. The catalyst was filtered off and the residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1 as eluents affording the title compound as a light yellow solid (85 mg).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. additionthe residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml)
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1 as eluents

Quellen und Nachweise

ORD-Eintrag
ord-3491cf4ea97b4ddc9009c139a53b6a32
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722695B2

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