Formaldehyde → 4-{[(2-Hydroxyethyl)(methyl)amino]methyl}-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 2423133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423133
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH2:6]=O.[CH3:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][N:16]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:12][C:11]=1[OH:28]>CCO>[OH:5][CH2:4][CH2:3][N:2]([CH2:6][C:12]1[C:11]([OH:28])=[C:10]([O:9][CH3:8])[CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH3:1]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 80162-(Methylamino)ethanolHCID 672416826-Methoxy-1-(phenylsulfonyl)-1H-indol-5-ol2×

Produkt 1

HCID 672402644-{[(2-Hydroxyethyl)(methyl)amino]methyl}-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-olAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 2-(methylamino)ethanol (0.37 g, 4.9 mmol) and paraformaldehyde (0.15 g, 4.9 mmol) was ethanol (5 mL) added. The reaction mixture was heated at 65° C. for 5 minutes and a clear solution was formed. 6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 15, 0.75 g, 2.5 mmol) in EtOH (10 mL) was added in one portion. The mixture was stirred for 2 hours at 70° C. The solvent was removed under reduced pressure and the crude material was dissolved in DCM and was washed with brine. The organic layer was collected and dried (MgSO4) to give the title compound (400 mg). MS m/z 391 [M+H]+.

Aufarbeitung

  1. additionadded
  2. customa clear solution was formed
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe crude material was dissolved in DCM
  5. washwas washed with brine
  6. customThe organic layer was collected
  7. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-9e389fb9d99e4de28d29265d6c26cb92
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960374B2

Notizen zur Reaktion

Wird geladen…