Water → 2-(4-Benzyloxy-2,5-difluoro-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 253389

Reaktionsgleichung

Reaktionsgleichung von HRID 253389
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12](Br)=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:23]([Si:26]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[N:27]1[C:31]2=[N:32][CH:33]=[CH:34][CH:35]=[C:30]2[C:29]([CH:36]=[O:37])=[CH:28]1)([CH3:25])[CH3:24].O>O1CCCC1.CCOCC>[CH2:1]([O:8][C:9]1[C:10]([F:17])=[CH:11][C:12]([C:28]2[N:27]([Si:26]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:39])[CH3:40])[CH:23]([CH3:25])[CH3:24])[C:31]3=[N:32][CH:33]=[CH:34][CH:35]=[C:30]3[C:29]=2[CH2:36][OH:37])=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 497589651H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-HCID 580861601-Benzyloxy-4-bromo-2,5-difluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 666786692-(4-Benzyloxy-2,5-difluoro-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 1-Benzyloxy-4-bromo-2,5-difluoro-benzene (47, 0.84 g, 2.80 mmol) in tetrahydrofuran (15.0 mL) and ether (15.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (1.20 mL, 2.50 M in hexane) was added slowly. After 20 minutes, 1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (8, 0.82 g, 0.0027 mol, prepared as described in Example 5) was added to the reaction. After 20 minutes, the reaction was allowed to warm to room temperature for 10 minutes, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified with silica gel column chromatography eluting with 20% ethyl acetate in hexane to a white solid (48, 10 g, 70.0%).

Aufarbeitung

  1. waitAfter 20 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified with silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane to a white solid (48, 10 g, 70.0%)

Quellen und Nachweise

ORD-Eintrag
ord-f529fc8d7c424f9882ee8c64b1804ab5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872018B2

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