Diisobutylaluminumhydride → N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

HRID 2170307

Reaktionsgleichung

Reaktionsgleichung von HRID 2170307
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11](N(OC)C)=[O:12])[C:8]([Br:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Br:17][C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:10][C:9]=1[CH:11]=[O:12]

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 902804776-acetamido-3-bromo-N-methoxy-N-methylpicolinamide

Produkt 1

HCID 90280237N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the crude material from last step (1B, 2.6 g, 8.6 mmol) in THF (tetrahydrofuran)(30 mL) was added DIBAL-H (diisobutylaluminium hydride)(13 mmol, 1.5 equiv) dropwise at 70° C. The reaction was stirred for 1 h and was then quenched with NH4Cl solution. The reaction mixture was partitioned between EtOAc and saturated NH4Cl solution. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was used in the next step without further purification. MS (m/z) 244.1 [M+H]+.

Aufarbeitung

  1. customwas then quenched with NH4Cl solution
  2. customThe reaction mixture was partitioned between EtOAc and saturated NH4Cl solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-2eb5869b1a384c52a45f79d471c447f1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050344B2

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