Ethyl Acetate → (3-Amino-6,7-dihydro-5H-furo[3,2-g]chromen-2-yl)-(3-methoxyl-phenyl)-methanone

HRID 856951

Reaktionsgleichung

Reaktionsgleichung von HRID 856951
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][C:3]=1[C:12]#[N:13].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19](=[O:22])[CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:13][C:12]1[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[O:1][C:20]=1[C:19]([C:18]1[CH:23]=[CH:24][CH:25]=[C:16]([O:15][CH3:14])[CH:17]=1)=[O:22])[O:9][CH2:8][CH2:7][CH2:6]3

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 218649727-Hydroxy-chroman-6-carbonitrile

Produkt 1

HCID 21864974(3-Amino-6,7-dihydro-5H-furo[3,2-g]chromen-2-yl)-(3-methoxyl-phenyl)-methanoneAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 7-Hydroxy-chroman-6-carbonitrile from method II-3 (30 mg, 0.17 mmol) and 3-methoxyphenacyl bromide (78.5 mg, 0.34 mmol, 2.0 eq) in anhydrous N,N-dimethylformamide (1.0 mL) was added potassium carbonate (47.3 mg, 0.34 mmol, 2.0 eq), and the orange reaction mixture was stirred at 100° C. for 17 h. The resulting dark wine colored reaction was poured into ethyl acetate (10 mL) and water (10 mL). This mixture was then extracted with EtOAc (2×10 mL). The combined organic layers were then dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified by pre-HPLC to afford the desired product as a yellow solid (30.7 mg, 54.9%). 1H-NMR (CD3CN) δ 7.73 (d, J=7.3 Hz, 1H), 7.66 (s, 1H), 7.50 (s, 1H), 7.44 (t, 1H), 7.34 (dd, J=2.8, 8.5 Hz, 1H), 6.80 (s, 1H), 4.25 (t, 2H), 3.89 (s, 3H), 2.93 (t, 2H), 2.03 (m, 2H); MS LC-MS (MH+=324).

Aufarbeitung

  1. customThe resulting dark wine colored reaction
  2. extractionThis mixture was then extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers were then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9887db0fb1264cad93871d007632ed44
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144885B2

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