Triacetoxyperiodinane → isobutane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-amide

HRID 217618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217618
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([OH:28])[C:12]3[C:13]([F:27])=[C:14]([NH:19][S:20]([CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([C:12]3[C:13]([F:27])=[C:14]([NH:19][S:20]([CH2:23][CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=3[F:18])=[O:28])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 595695972-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide

Produkt 1

HCID 59569619isobutane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-amideAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a round bottom flask, 2-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide (68, 618 mg, 1.30 mmol) was dissolved in 20 mL of tetrahydrofuran, and Dess-Martin periodinane (555 mg, 1.31 mmol) was added. The reaction was stirred at room temperature for 30 minutes, then quenched with water and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate, water, and brine, then dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with dichloromethane and methanol. Appropriate fractions were collected and concentrated under vacuum to provide the desired compound (69, 257 mg). MS (ESI) [M−H+]−=469.9, 471.9.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with sodium bicarbonate, water, and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with dichloromethane and methanol
  9. customAppropriate fractions were collected
  10. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b6f942ea4404409891e5b78b28c9dece
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198273B2

Notizen zur Reaktion

Wird geladen…