Sodium hydride → HCID 19385711, compound

HRID 1492596Notes

Reaction equation

HRID 1492596 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][CH2:22][CH3:23])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:24])[CH:3]=1.[H-].[Na+].[H][H].Br[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][C:37]([O:39][CH3:40])=[O:38]>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:36]([C:37]([O:39][CH3:40])=[O:38])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:30]=4)=[C:16]([CH2:21][CH2:22][CH3:23])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 19385672HCID 19385672, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19385711HCID 19385711, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.062 g (0.19 mmol) of the product of Step A in 1.5 mL of anhydrous DMF was added 8.4 mg of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere. After the reaction mixture had stirred 30 minutes at room temperature, hydrogen evolution had ceased, and a solution of 0.048 g of methyl 2-bromophenylacetate in 0.5 mL of dry DMF was added via syringe. The reaction mixture was stirred an additional 1.5 hours and then partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered, evaporated and then chromatographed on a silica gel flash chromatography column eluted with 50% ethyl acetate-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 59 mg (66%) of the title compound as a viscous oil.

Workup

  1. stirringAfter the reaction mixture had stirred 30 minutes at room temperature
  2. stirringThe reaction mixture was stirred an additional 1.5 hours
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed on a silica gel flash chromatography column
  10. washeluted with 50% ethyl acetate-hexane
  11. customevaporated
  12. customdried in vacuo

Sources & evidence

ORD record
ord-26795823b22c46bdafeb913fffe912d7
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…