4-(Bromomethyl)benzene-1,2-dicarbonitrile → HCID 18779782, compound

HRID 1421764Notes

Reaction equation

HRID 1421764 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:11]#[N:12])[C:6](=[CH:9][CH:10]=1)[C:7]#[N:8].[Cl:13][C:14]1[CH:15]=[CH:16][C:17](=[O:51])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]3[N:28]=[CH:29][N:30](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:31]=3)=[CH:22][N:21]=2)[CH:19]=1>CC#N>[Cl:13][C:14]1[CH:15]=[CH:16][C:17](=[O:51])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]3[N:28]([CH2:2][C:3]4[CH:4]=[C:5]([C:11]#[N:12])[C:6](=[CH:9][CH:10]=4)[C:7]#[N:8])[CH:29]=[N:30][CH:31]=3)=[CH:22][N:21]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 187797764-(Bromomethyl)benzene-1,2-dicarbonitrileHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 18779782HCID 18779782, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Bromomethyl-phthalonitrile from step 3 (50 mg, 0.28 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (150 mg, 0.28 mmol) were dissolved in CH3CN (1.4 ml) and heated to 60° C. for 16 hours. The solvent was removed in vacuo and redissolved in MeOH (1.4 ml). The reaction mixture was heated to 60° C. for several hours. Solvent was removed in vacuo and the resulting residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2 ] to yield the final product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionredissolved in MeOH (1.4 ml)
  3. temperatureThe reaction mixture was heated to 60° C. for several hours
  4. customSolvent was removed in vacuo
  5. customthe resulting residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2 ]

Sources & evidence

ORD record
ord-20218999fa704685ba1724a058dee1ec
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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