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Hydrochloric Acid → 2-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamide

HRID 1404138
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1404138
C([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15](Br)=[C:14]2[C:10]=1[C:11]([CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[CH:12][N:13]2[CH3:20])C1C=CC=CC=1.N1C=CC=CC=1.Cl>CO.[Pd]>[F:18][C:17]1[C:9]([OH:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:20])[CH:12]=[C:11]2[CH2:21][C:22]([NH:24][CH3:25])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 583040222-(4-(benzyloxy)-7-bromo-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide

Produkt 1

HCID 583040072-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A mixture of 33-5 (1.4 g, 4.5 mmol), pyridine (2 mL) and Pd/C (140 mg, 10%) in methanol (20 mL) was stirred at room temperature overnight under hydrogen atmosphere. The mixture was adjusted with hydrochloric acid to pH=5-6. The solid was filtered off and the filtrate was concentrated. The resulting residue was partitioned between water (20 mL) and ethylacetate (20 mL). The organic layer was separated, washed with brine (3×30 mL), dried over MgSO4, filtered and evaporated to obtain 33-6 (700 mg, 85%) as a brown solid. LRMS: calc 236.1 and found: 237.1 [M+1].

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was partitioned between water (20 mL) and ethylacetate (20 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (3×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-359afddcd28b4008b201347ecfc3b8d5
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08912220B2

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