Sodium hydride → 6-Chloro-2-isobutoxy-nicotinamide

HRID 1255749Notes

Reaction equation

HRID 1255749 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].ClC1C=[CH:20][C:16]([C:17](N)=[O:18])=[C:15](OCCC)N=1.[H-].[Na+]>C(#N)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([O:18][CH2:17][CH:16]([CH3:20])[CH3:15])[N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 221427782,6-Dichloropyridine-3-carboxamideHCID 579687006-Chloro-2-propoxy-nicotinamide

Product 1

HCID 579689596-Chloro-2-isobutoxy-nicotinamideYield 66.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,6-dichloro-nicotinamide (1) (3 g, 15.7 mmol) in acetonitrile (anhydrous, 30 mL) were added 2-methyl-propan-1-ol (2) (1.22 g, 16.5 mmol) and NaH (0.42 g, 16.5 mmol). The reaction was kept at r.t. O/N. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by Biotage silica gel chromatography with 10%-80% EtOAc/hexanes gradient elution to afford 2.39 g (66% yield) of the title compound.

Workup

  1. customwas kept at r.t
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by Biotage silica gel chromatography with 10%-80% EtOAc/hexanes gradient elution

Sources & evidence

ORD record
ord-45f951ad0c3345d188a98650203f8ad9
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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