Diisobutylaluminumhydride → N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide

HRID 931626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931626
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1[C:8]([F:13])=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([CH2:25][C:26](OC(C)(C)C)=[O:27])[NH:18][S:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1[C:8]([F:13])=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([NH:18][S:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])[CH2:25][CH2:26][OH:27]

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 86658360tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate

Produkt 1

HCID 86658362N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate (7.5 g, 13.69 mmol) in dry THF (25 mL) was cooled to −78° C. and diisobutylaluminum hydride (54.8 mL, 54.8 mmol) was added drop wise. The mixture was warmed to 0° C. and kept at this temperature for 1 h. The reaction mixture was quenched with a aqueous, saturated solution of Rochelle's salt and vigorously stirred for 15 h. The organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solution was concentrated under reduced pressure. The residue was purified by chromatography (0-30% EtOAc/hexanes) to afford N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide (5.8 g, 89% yield) as a light yellow solid.

Aufarbeitung

  1. customThe reaction mixture was quenched with a aqueous, saturated solution of Rochelle's salt
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe solution was concentrated under reduced pressure
  7. customThe residue was purified by chromatography (0-30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-04d1dbc3b33f490095131957a57aa97a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296759B2

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