Sodium hydride → HCID 19385708, compound

HRID 1492593Notes

Reaction equation

HRID 1492593 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH2:21][CH:22]=[CH2:23])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:24])[CH:3]=1.[H-].[Na+].Br[CH:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[C:29]([CH:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:24])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:15][C:16]=1[CH2:21][CH:22]=[CH2:23])([O:31][CH3:32])=[O:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 19385668HCID 19385668, compound

Product 1

HCID 19385708HCID 19385708, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.17 1 g (0.53 mmol) of the product of Step G dissolved in 2.5 mL of anhydrous DMF was added 0.023 g (0.58 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere for 30 minutes at room temperature. A solution of 0.134 g of methyl α-bromophenylacetate in 1.0 mL of DMF was then added via syringe and the reaction mixture was stirred an additional 1.5 hours. The reaction mixture was then partitioned between ethyl acetate and water, the organic layer was separated, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 75% ethyl acetate-hexane to afford after evaporation of the purified fractions and drying in vacuo 0.212 g (85%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred an additional 1.5 hours
  2. customThe reaction mixture was then partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual oil was purified on a silica gel flash chromatography column
  8. washeluted with 75% ethyl acetate-hexane
  9. customto afford
  10. customafter evaporation of the purified fractions
  11. dry with materialdrying in vacuo 0.212 g (85%) of the title compound

Sources & evidence

ORD record
ord-e02a08b00fc14e8da7692180fd4f74bc
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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