2-Chloro-4-cyanopyridine → 2-(1-Methylimidazol-4-yl)pyridine-4-carbonitrile

HRID 2277437Notes

Reaction equation

HRID 2277437 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][N:11]1[CH:15]=[C:14]([Sn](CCCC)(CCCC)CCCC)[N:13]=[CH:12]1>C1(C)C=CC=CC=1>[CH3:10][N:11]1[CH:15]=[C:14]([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)[N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 219011411-Methyl-4-(tributylstannyl)-1H-imidazole

Product 1

HCID 904075092-(1-Methylimidazol-4-yl)pyridine-4-carbonitrileYield 62.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloro-4-pyridinenitrile (300 mg, 2.16 mmol) in toluene (10 mL) was added N-methyl-4-(tributylstannyl)imidazole (964 mg, 2.6 mmol), followed by tetrakistriphenylphosphine palladium (0) (150 mg, 0.13 mmol). The reaction mixture was heated at 120° C. in a microwave initiator for 1 hr. The mixture was cooled down to r.t, solid filtered and dried to give 250 mg of 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile as a white solid. Filtrate was purified by flash column chromatography (CH2Cl2/MeOH=20/1) to give additional 100 mg of the product (total 350 mg, 88%). 1H NMR (400 MHz, DMSO-d6): δ 3.73 (3H, s), 7.59 (1H, d, J=4.8 Hz), 7.82 (1H, s), 8.09 (1H, s), 8.72 (1H, d, J=5 Hz). [M+H] Calc'd for C10H8N4, 185. Found, 185.

Workup

  1. temperatureThe mixture was cooled down
  2. filtrationsolid filtered
  3. customdried

Sources & evidence

ORD record
ord-5444fb8878574e2192e0729f4d138bf7
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

Loading…