6-Methylpyridine-2-carbonitrile → HCID 63788697, compound

HRID 60804Notes

Reaction equation

HRID 60804 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:11](=[O:10])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 741826-Methylpyridine-2-carbonitrileHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 63788697HCID 63788697, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-methyl-2-cyanopyridine (5 g) and BOC2O in EtOAc was added 10% Pd/C. The reaction mixture was stirred under a balloon of H2 for 24 h, and then filtered through diatomaceous earth and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (EtOAc/hex) to give the title compound as a colorless oil. 1H NMR (d6-DMSO, 400 MHz) δ 7.6 (t, 1H), 7.4 (br s, NH), 7.2 (d, 1H), 7.1 (d, 1H), 4.2 (d, 2H), 2.4 (s, 3H), 1.4 (s, 9H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by chromatography on silica gel (EtOAc/hex)

Sources & evidence

ORD record
ord-4fe63c80ffb9415586e42900725fb1c6
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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