Diisobutylaluminum hydride → 4-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

HRID 1177559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177559
CC(C[AlH]CC(C)C)C.[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([C:32]#N)=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(C(C(C([O-])=O)O)O)([O-])=[O:37]>C(Cl)Cl>[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([CH:32]=[O:37])=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 671129224-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile

Produkt 1

HCID 866387254-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

DIBAL-H (1.0M in hexanes) (185 μl, 0.185 mmol) was added to a solution of 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile (59.6 mg, 0.169 mmol) in DCM (2.7 mL) at 25° C., and the resulting solution was stirred at 25° C. for 45 min. Sat. aq. Na/K tartrate solution (3.0 mL) was added, and the resulting mixture was vigorously stirred for 15 min, then partitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes) provided 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde as a light yellow solid. MS (ESI) m/z: Calculated: 356.1; Observed: 357.1 (M++1).

Aufarbeitung

  1. stirringthe resulting mixture was vigorously stirred for 15 min
  2. custompartitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e038ce7cd8904649962cfcd546d09d44
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

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