Sodium hydride → HCID 70153777, compound

HRID 2179969Notes

Reaction equation

HRID 2179969 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C@H:10]([C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)[OH:11])([CH3:4])[CH3:3].[Cl:18][C:19]1[C:26]([F:27])=[CH:25][C:22]([C:23]#[N:24])=[C:21](F)[CH:20]=1.[H-].[Na+]>CN(C)C=O>[CH3:4][C:2]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C@@H:10]([O:11][C:21]1[CH:20]=[C:19]([Cl:18])[C:26]([F:27])=[CH:25][C:22]=1[C:23]#[N:24])[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 86759700HCID 86759700, compound

Product 1

HCID 70153777HCID 70153777, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step (b) (277 mg, 1.15 mmol) and 4-chloro-2,5-difluorobenzonitrile (199 mg, 1.15 mmol) were dissolved in dimethylformamide (10 ml) and sodium hydride (60%, 48 mg, 1.2 mmol) added in one portion. The reaction was stirred for 2 h at room temperature then quenched with aqueous saturated ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×60 ml). The combined organic extracts were washed with water (3×20 ml), dried (sodium sulphate) and evaporated iii vacuo. The residue was chromatographed on flash silica, eluting with hexane:ethyl acetate (3:1), to give the title compound as a white crystalline solid (330 mg, 73%).

Workup

  1. customthen quenched with aqueous saturated ammonium chloride solution (30 ml)
  2. extractionextracted with ethyl acetate (3×60 ml)
  3. washThe combined organic extracts were washed with water (3×20 ml)
  4. dry with materialdried (sodium sulphate)
  5. customevaporated iii vacuo
  6. customThe residue was chromatographed on flash silica
  7. washeluting with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-31020b2b24334142b77c80e5b5e6d693
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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