Dimethylformamide → HCID 18698779, compound

HRID 2289639Notes

Reaction equation

HRID 2289639 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21](Cl)[N:20]=4)[C:15](=[O:26])[CH:14]=3)[CH:10]=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:29][N:30](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21]([C:29]#[N:30])[N:20]=4)[C:15](=[O:26])[CH:14]=3)[CH:10]=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6228Dimethylformamide2×HCID 18698784HCID 18698784, compound

Product 1

HCID 18698779HCID 18698779, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 4-[5-(4-Bromophenoxy)imidazol-1-ylmethyl]-1-(6-chloropyrazin-2-yl)-1H-pyridin-2-one (79 mg, 0.17 mmol) and zinc cyanide (12 mg, 0.1 mmol) in DMF (1 mL) was purged with argon for 5 min. A solution of tetrakis(triphenylphosphine)palladium(0) (20 mg, 17 μmol) in DMF (0.5 mL) was added. The resultant mixture was stirred under argon at 80° C. overnight, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1:1 v/v 5% methanol in chloroform and chloroform saturated with ammonia gas. Collection, concentration of appropriate fractions, and trituration of the residue with anhydrous ether provided the titled compound as white solid.

Workup

  1. customwas purged with argon for 5 min
  2. concentrationconcentrated under vacuum
  3. customCollection, concentration of appropriate fractions, and trituration of the residue with anhydrous ether

Sources & evidence

ORD record
ord-0821e3860b5441d48ca8bc35d1671e3f
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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