Diisobutylaluminum hydride → 3-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177474
CC(C[AlH]CC(C)C)C.[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29]1)[N:22]=2)[C:14]#N.C(C(C(C([O-])=O)O)O)([O-])=[O:38]>C(Cl)Cl>[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29]1)[N:22]=2)[CH:14]=[O:38]

Komponenten

5

Edukt 3

HCID 14487Diisobutylaluminum hydride2×HCID 38061142,3-DihydroxybutanedioateHCID 671116823-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile

Produkt 1

HCID 866387133-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

DIBAL-H (11.0M in hexanes; 0.315 mL, 0.315 mmol) was added to a solution of 3-methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile (105.2 mg, 0.286 mmol) in CH2Cl2 (4.5 mL) at 25° C., and the resulting solution was stirred at 25° C. for 45 min. Additional DIBAL-H (1.0M in hexanes; 86 μL, 86 μmol) was then added, and the resulting solution was stirred at 25° C. for 30 min. Saturated aqueous Na/K tartrate solution (4.0 mL) was added, and the resulting mixture was vigorously stirred for 15 min, then partitioned between CH2Cl2 (40 mL) and saturated aqueous Na/K tartrate solution (10 mL). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-40% EtOAc/hexanes) provided 3-methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde as a light-yellow foam. MS (ESI) m/z: Calculated: 370.1; Observed: 371.1 (M++1).

Aufarbeitung

  1. stirringthe resulting solution was stirred at 25° C. for 30 min
  2. stirringthe resulting mixture was vigorously stirred for 15 min
  3. custompartitioned between CH2Cl2 (40 mL) and saturated aqueous Na/K tartrate solution (10 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customChromatographic purification of the residue (silica gel, 0-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fc294d335aca442388111f2d70971b89
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

Notizen zur Reaktion

Wird geladen…