Dichloromethane → 3-(5-Thiophen-3-yl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol

HRID 562847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562847
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1.C(Cl)Cl.B(Br)(Br)Br>O>[S:18]1[CH:19]=[CH:20][C:16]([C:13]2[CH:14]=[C:15]3[C:7]([CH2:6][C:5]4[CH:4]=[C:3]([OH:2])[CH:23]=[CH:22][CH:21]=4)=[CH:8][NH:9][C:10]3=[N:11][CH:12]=2)=[CH:17]1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 111629973-(3-Methoxy-benzyl)-5-thiophen-3-yl-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 113012233-(5-Thiophen-3-yl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenolAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a Round bottom flask was added compound 14 (20.0 mg, 0.0000624 mol) and Methylene chloride (4.0 mL, 0.062 mol) at room temperature. Into the reaction mixture, was added 0.1 mL BBr3 (1.0M in). The reaction mixture was allowed to room temperature for 5 hours. TLC indicated the reaction was not complete. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with preparative TLC to give product 15 (5 mg).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-fa63e1ea626e4147af0cff703b7be438
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067434B2

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