Ethyl Acetate → HCID 18535989, compound

HRID 2306260Notes

Reaction equation

HRID 2306260 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][C:4]=1[F:11])#[N:2].[CH:12]([C:14]1[N:15]=[C:16]([CH3:19])[NH:17][CH:18]=1)=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:15]2[C:14]([CH:12]=[O:13])=[CH:18][N:17]=[C:16]2[CH3:19])=[CH:5][C:4]=1[F:11])#[N:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27784664-Cyano-3-fluorobenzyl bromideHCID 178418999HCID 178418999, compound

Product 1

HCID 18535989HCID 18535989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyano-3-fluorobenzyl bromide, as described in Example 1, Step D, (1.26 g, 5.9 mmol) in DMF (10 mL), at 0° C., was added 4-formyl-2-methylimidazole (0.650 g, 5.9 mmol) and cesium carbonate (2.9 g, 8.9 mmol). After 2 hours, the reaction mixture was poured into EtOAc—30% hexane, washed with H2O, then brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide the crude product. The crude material was purified by silica gel chromatography, eluting with a gradient of CHCl3—2% to 5% MeOH, to obtain the above-titled product.

Workup

  1. washwashed with H2O
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a gradient of CHCl3—2% to 5% MeOH

Sources & evidence

ORD record
ord-df516ef6de8c4e58be848fd48ff7247c
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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