Tetrahydrofuran → propane-1-sulfonic acid (2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl)-amide

HRID 60102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60102
[F:1][C:2]1[C:7]([CH:8]([OH:27])[C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([B:18]4[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]4)[CH:16]=3)[NH:11][CH:10]=2)=[C:6]([F:28])[CH:5]=[CH:4][C:3]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31].O1CCCC1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([B:18]4[O:19][C:20]([CH3:25])([CH3:26])[C:21]([CH3:23])([CH3:24])[O:22]4)[CH:16]=3)[NH:11][CH:10]=2)=[O:27])=[C:6]([F:28])[CH:5]=[CH:4][C:3]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:31])=[O:32]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 58368760propane-1-sulfonic acid (2,4-difluoro-3-{hydroxy-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-phenyl)-amide

Produkt 1

HCID 58368878propane-1-sulfonic acid (2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a reaction flask, propane-1-sulfonic acid (2,4-difluoro-3-{hydroxy-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-phenyl)-amide (29, 0.155 g, 0.306 mmol) is combined with 10 mL of tetrahydrofuran and 3 mL of dichloromethane. Dess-Martin periodinane (0.648 g, 1.53 mmol) is added and the reaction is stirred at room temperature for 20 minutes. The reaction is mixed with 1N sodium thiosulfate, extracted with ethyl acetate and the organic layer dried and purified by silica gel column chromatography, eluting with a gradient of 20-100% ethyl acetate in hexanes. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=506.29.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customthe organic layer dried
  3. custompurified by silica gel column chromatography
  4. washeluting with a gradient of 20-100% ethyl acetate in hexanes
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-478ac231d31f45eba141dc915f7d3d96
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440969B2

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