Ethyl bromoacetate → Ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate

HRID 229458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229458
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].CCOC(C)=O>CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[C:12]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:8]=1)(=[O:16])[CH:13]([CH3:14])[CH3:15]

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 588238251-(6-methoxy-1H-indazol-3-yl)-2-methylpropan-1-one

Produkt 1

HCID 86618180Ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 10796Cesium carbonateLösungsmittel

Versuchsvorschrift

Dissolve 5.456 g of 1-(6-methoxy-1H-indazol-3-yl)-2-methylpropan-1-one in 100 mL anhydrous DMF. Weigh in 8.96 g cesium carbonate followed by 4.593 g ethyl bromoacetate. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. Partition the residue between EtOAc and water. Extract the aqueous layer with EtOAc several times. The combined organic extract was washed with water (3×) and saturated brine, dried over anhydrous Na2SO4, and evaporated to give the crude product. The title compound was obtained by recrystallization from 40 mL 4:1 hexanes and EtOAc. 1H NMR (CDCl3, 500 MHz) δ 8.26 (d, 8.9 Hz, 1H), 7.00 (dd, 2.1 & 9.0 Hz, 1H), 6.685 (d, 2.1 Hz, 1H), 5.17 (s, 2H), 4.28 (q, 7.1 Hz, 2H), 3.90 (s, 3H), 3.87 (heptet, 6.9 Hz, 1H), 1.29 (t, 7.1 Hz, 3H), 1.28 (d, 6.8 Hz, 6H). LC-MS: 3.51 min. (m/Z=305.1, 327.0).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customPartition the residue between EtOAc and water
  3. extractionExtract the aqueous layer with EtOAc several times
  4. extractionThe combined organic extract
  5. washwas washed with water (3×) and saturated brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-61b7c45b7a3d44cc8f95aa2962e2dba1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563816B2

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