Sodium hydride → HCID 86617111, compound

HRID 1723699Notes

Reaction equation

HRID 1723699 reaction equation
[N:1]([C@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@@H:5]1[NH:16][C:17](=[O:25])[CH2:18][CH2:19][C:20]([F:24])([F:23])[CH2:21]Br)=[N+:2]=[N-:3].[H-].[Na+]>CN(C)C=O>[N:1]([C@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@@H:5]1[N:16]1[CH2:21][C:20]([F:24])([F:23])[CH2:19][CH2:18][C:17]1=[O:25])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86617110HCID 86617110, compound

Product 1

HCID 86617111HCID 86617111, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step 6 (22.0 g, 52.8 mmol) in N,N-dimethylformamide (220 mL) was added sodium hydride (60% suspension in mineral oil, 3.38 g, 84.6 mmol) in several portions. The reaction was stirred at room temperature for 16 hours and then ice water (50 mL) was added slowly. The resulting mixture was partitioned between ethyl acetate and H2O and the organic phase washed with 2% aqueous lithium chloride solution and then brine. The organic layer was dried over sodium sulfate and concentrated to an oil that was separated by silica gel chromatography (75M Biotage Si1 (A Dynax Corp.; Charlottesville, Va.) eluting with a pentane/EtOAc gradient (4:1-1:1) to afford 17.7 g (53%) of the product as a solid. MS m/z 336.3 (AP+100).

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate and H2O
  2. washthe organic phase washed with 2% aqueous lithium chloride solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to an oil that
  5. customwas separated by silica gel chromatography (75M Biotage Si1 (A Dynax Corp
  6. wash) eluting with a pentane/EtOAc gradient (4:1-1:1)

Sources & evidence

ORD record
ord-26d5d1f266db4a7bb2c66e558772466e
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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