Hydrogen Bromide → 1-Methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-ol

HRID 1765565

Reaktionsgleichung

Reaktionsgleichung von HRID 1765565
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[NH:21][C:16]2=[N:17][CH:18]=[CH:19][N:20]=[C:15]2[CH:14]=1.Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[C:6]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=2)=[CH:7]1

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 98604486-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 224772321-Methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-olAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [200 mg, Example 1(a)] hydrobromic acid (48%, 500 μl) and glacial acetic acid (3 mL) was heated under reflux for 14 hours. After cooling the mixture was neutralised by addition of saturated sodium bicarbonate solution. The resulting dark solid was filtered and then dried to give the title compound (180 mg) as a black solid, m.p. 289–290° C. MS: 264 (MH+).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 14 hours
  3. temperatureAfter cooling the mixture
  4. filtrationThe resulting dark solid was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-038ed65e7d074117a6a63e671b14adba
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07227020B2

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