Isobutyramide → HCID 29921637, compound

HRID 554767Notes

Reaction equation

HRID 554767 reaction equation
BrC1[CH:3]=[N:4]C=C(C=1)C(O)=O.Br[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:24]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CC(C)C(N)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Zn]>[C:3]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:24]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])#[N:4]

Participants

8

Reactant 3

HCID 68424IsobutyramideHCID 887075-Bromonicotinic acidHCID 18422124tert-Butyl 5-bromonicotinate

Product 1

HCID 29921637HCID 29921637, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 15826098HCID 15826098, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Instead of the starting material of Reference Example 56, that is, the compound S55, the 5-bromonicotinic acid was used for the similar procedure as in Reference Example 56. To the obtained tert-butyl 5-bromonicotinate (22.4 g), dimethylacetoamide (112 ml), tris(dibenzylideneacetone)dipalladium (1.59 g), zinc cyanide (6.1 g), diphenylphosphinoferrocene (1.92 g), and zinc powder (0.68 g) were added and the mixture was stirred under argon atmosphere at 120° C. for 1.5 hours. The reaction solution was filtered by sellite, which was then washed with ethyl acetate, and the filtrate was washed with saturated saline. The organic layer was dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain tert-butyl 5-cyanonicotinate (13.1 g).

Workup

  1. filtrationThe reaction solution was filtered by sellite, which
  2. washwas then washed with ethyl acetate
  3. washthe filtrate was washed with saturated saline
  4. dry with materialThe organic layer was dried over with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-f58ad093509a4dd39e2b73cc8e2e5615
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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