6-Fluoro-1-methyl-1H-indole-3-carbaldehyde → Methyl (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate

HRID 1372760

Reaktionsgleichung

Reaktionsgleichung von HRID 1372760
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]=[O:13])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[O:13][C:16]4[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=4[N:14]=3)=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 64981976-Fluoro-1-methyl-1H-indole-3-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Produkt 1

HCID 58778430Methyl (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In ethanol (15 ml), 6-fluoro-1-methylindole-3-carbaldehyde (500 mg, 2.82 mmol) and methyl 4-amino-3-hydroxyphenylacetate (767 mg, 4.23 mmol) were stirred at room temperature for 2 hours. Iodobenzene diacetate (1.09 g, 3.38 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then distilled under reduced pressure to remove the solvent. The residue was purified chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:1, v/v) eluate fractions, methyl (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate (889 mg, 93%) was obtained as a brown solid.

Aufarbeitung

  1. distillationThe reaction mixture was then distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:1

Quellen und Nachweise

ORD-Eintrag
ord-97a2e736cd95465483e564c7eb34cdf4
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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