Morpholine → 2-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)-1-morpholinoethanone

HRID 1404099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404099
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([CH2:14][C:15]([OH:17])=O)=[CH:4]1)[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([CH2:14][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[CH:4]1)[CH3:2]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 583039722-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)acetic acid

Produkt 1

HCID 583040262-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)-1-morpholinoethanoneAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compounds 11-3 (119 mg, 0.5 mmol) in DMF (2 mL) was added morpholine (66 uL, 0.75 mmol), triethylamine (0.24 mL, 1.75 mmol) and BOP (265 mg, 0.6 mmol). The reaction mixture was stirred at room temperature overnight. The solution was diluted with water and extracted with EtOAc. Combined organic layers were washed with 1N HCl, water, brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (silica gel, ethyl acetate:hexanes: 25:75 to 100%) gave pure 11-4 (140 mg, 91%) as a white foam.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washCombined organic layers were washed with 1N HCl, water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (silica gel, ethyl acetate:hexanes: 25:75 to 100%)

Quellen und Nachweise

ORD-Eintrag
ord-54c252789ac54488855cdf85c131c9fd
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912220B2

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