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

HRID 2170307

Reaction equation

HRID 2170307 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-2eb5869b1a384c52a45f79d471c447f1
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Linked notes

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