Water → 1-(Toluene-4-sulfonyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine

HRID 269511

Reaktionsgleichung

Reaktionsgleichung von HRID 269511
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH2:21](OB(C=C)OCCCC)[CH2:22]CC.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([CH3:20])[CH:18]=[CH:19][C:14]([S:11]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([CH:21]=[CH2:22])[CH:3]=[C:4]3[CH:10]=[CH:9]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-

Produkt 1

HCID 598322871-(Toluene-4-sulfonyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, (300 mg, 0.85 mmol), vinylboronic acid dibutylester, (184 mg, 1.0 mmol), potassium carbonate, (420 mg, 3.0 mmol) and Pd(Ph3P)4 were combined in 3 mL DME and 1 mL water in a tube under nitrogen and heated in a microwave reactor to 130° C. for 10 min. The organic layer was then separated and evaporated. The residue was purified by silica chromatography (eluent: methylene chloride), affording 215 mg(85%) 1-(Toluene-4-sulfonyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine. MS ES+ 299.0.

Aufarbeitung

  1. customThe organic layer was then separated
  2. customevaporated
  3. customThe residue was purified by silica chromatography (eluent: methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-24f416e6f4e84c9db95573211c416b6a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446199B2

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