Triethylamine → 2-((1-cyclopropyl-2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)methyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-6-carbonitrile

HRID 632859Notes

Reaction equation

HRID 632859 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:8]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]2=[N:6][CH:7]=1.[C:30]([Zn]C#N)#[N:31].C(N(CC)CC)C>O1CCOCC1>[CH:21]1([N:14]2[C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[N:12]([CH2:11][C:9]3[N:8]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]4=[N:6][CH:7]=[C:2]([C:30]#[N:31])[CH:3]=[C:4]4[N:10]=3)[C:13]2=[O:24])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 679917843-((6-bromo-3-isopentyl-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-oneHCID 178514179HCID 178514179, compound

Product 1

HCID 573788812-((1-cyclopropyl-2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)methyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of compound 16 (0.5 g, 1 mmol), Dichloro(diphenylphosphinoferrocene)palladium (78.7 mg, 0.108 mmol), dicyanozinc (0.505 g, 4.3 mmol) and triethyl amine (0.6 mL, 4.3 mmol) in dioxane (10 mL) under nitrogen atmosphere was irradiated for 1 h in a microwave reactor at 125° C. The resulting mixture was allowed to cool down to room temperature then filtered over dicalite. The filtrate was evaporated to dryness. The pεσιδνε was purified by column chromatography using EtOAc/MeOH 8-2. The title compound 27 was isolated as a white solid (200 mg, 45%). m/z=402 (M+H)+.

Workup

  1. customwas irradiated for 1 h in a microwave reactor at 125° C
  2. filtrationthen filtered over dicalite
  3. customThe filtrate was evaporated to dryness
  4. customThe pεσιδνε was purified by column chromatography

Sources & evidence

ORD record
ord-eb70c583ad7d401ba8c780c590de9840
Source dataset
uspto-grants-2016_04
Patent number
US09321767B2

Reaction notes

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