4-Bromo-1H-indole-3-carbaldehyde → 4-Bromo-3-methyl-1H-indole

HRID 1159777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159777
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH:17]=O)=[CH:11][NH:12]2>C1COCC1>[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH3:17])=[CH:11][NH:12]2

Komponenten

4

Edukt 2

HCID 27631784-Bromo-1H-indole-3-carbaldehyde2×HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 529877044-Bromo-3-methyl-1H-indoleAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LAH (1.0M in THF, 5.75 mL, 5.75 mmol) was added dropwise to refluxing 4-bromo-1H-indole-3-carbaldehyde (644 mg, 2.87 mmol; Intermediate 27) in dry THF (20 mL). The mixture was refluxed 1 h, allowed to attain rt. and quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL). The resulting precipitation was filtered off, the filtrate concentrated and the residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL). The organic layers were combined with combined with an earlier batch of this intermediate (followed this experimental and starting from 4-bromo-1H-indole-3-carbaldehyde, 100 mg, 0.45 mmol; Intermediate 27), dried and concentrated to give the title compound (556 mg, 80%) as a light brown oil. MS (ESI+) for C9H8BrN m/z 210 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was refluxed 1 h
  2. customto attain rt
  3. customand quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL)
  4. customThe resulting precipitation
  5. filtrationwas filtered off
  6. concentrationthe filtrate concentrated
  7. extractionthe residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL)
  8. dry with materialIntermediate 27), dried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-93ec121d0840423bbab25d5c676b2366
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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