Sodium hydride → HCID 57444583, compound

HRID 2250641Notes

Reaction equation

HRID 2250641 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([C:14]2[NH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[NH2:23]OP(=O)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O>[NH2:23][N:15]1[C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=[C:14]1[C:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([Br:1])[CH:11]=1)=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 57444580HCID 57444580, compound

Product 1

HCID 57444583HCID 57444583, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-bromo-4-[(5-ethyl-1H-pyrrol-2-yl)carbonyl]benzoate (330 mg) in N,N-dimethylformamide (5 mL) was added 60% sodium hydride in oil (58.4 mg) in an ice-bath over 5 minutes. After stirring for 1 hour, (aminooxy)(diphenyl)phosphine oxide (340 mg) was added portionwise over 40 minutes. The resulting mixture was stirred for 1 hour in the bath. The reaction was quenched by adding water (10 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water (two times) and brine, dried over magnesium sulfate, and evaporated. The residue was dissolved in ethyl acetatec-hexane (1-5), and to the solution was added silica gel. The mixture was filtered, and the filtrate was evaporated to give methyl 4-[(1-amino-5-ethyl-1H-pyrrol-2-yl)carbonyl]-2-bromobenzoate as an orange solid (310 mg).

Workup

  1. stirringThe resulting mixture was stirred for 1 hour in the bath
  2. customThe reaction was quenched
  3. additionby adding water (10 mL)
  4. customThe mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water (two times) and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. dissolutionThe residue was dissolved in ethyl acetatec-hexane (1-5)
  9. additionto the solution was added silica gel
  10. filtrationThe mixture was filtered
  11. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-33b76342d07b4af39b5963eabcb1b4fb
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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