4-Bromomethyl-2-(2,2,2-trifluoro-ethoxy)-benzonitrile → 4-[5-(5-Chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-(2,2,2-trifluoro-ethoxy)-benzonitrile

HRID 1421741Notes

Reaction equation

Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH:4]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21](=[O:55])[N:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[N:32]=[CH:33][N:34](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:35]=3)=[CH:26][N:25]=2)[CH:23]=1>CC#N>[Cl:17][C:18]1[CH:19]=[CH:20][C:21](=[O:55])[N:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[N:32]([CH2:2][C:3]4[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH:4]=4)[CH:33]=[N:34][CH:35]=3)=[CH:26][N:25]=2)[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Bromomethyl-2-(2,2,2-trifluoro-ethoxy)-benzonitrile from Step 3 (200 mg, 0.68 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (360 mg, 0.68 mmol) were dissolved in CH3CN (3.5 ml) and heated to 60° C. for 4 hours. The solvent was removed in vacuo and redissolved in MeOH (3.5 ml). The reaction mixture was heated to 60° C. for 3 more hours. The solvent was removed in vacuo and the crude residue purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2) to yield the final product.

Workup

customThe solvent was removed in vacuo
dissolutionredissolved in MeOH (3.5 ml)
temperatureThe reaction mixture was heated to 60° C. for 3 more hours
customThe solvent was removed in vacuo
customthe crude residue purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2)

Sources & evidence

ORD record: ord-259c6c6574fb44219aa61ad80db5f1e4
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06077853

Reaction notes

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