1-Benzoyl-2-isopropylhydrazine → HCID 58689900, compound

HRID 2250894Notes

Reaction equation

HRID 2250894 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH:15]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([N:18]([CH:15]([CH3:17])[CH3:16])[NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:8]

Participants

6

Reactant 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 58689903904297-95-6

Product 1

HCID 58689900HCID 58689900, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-bromo-4,5-difluoro-phenoxy)-acetic acid (985 mg, 3.68 mmol) and benzoic acid N′-isopropyl-hydrazide (787 mg, 4.416 mmol) in DMF (20 mL) was treated with diisopropylethyl amine (1.6 mL, 9.2 mmol) and PyBroP (2.57 g, 5.52 mmol) at room temperature overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was successively washed with saturated sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-30% ethyl acetate/hexanes gradient to afford the product as a white solid (832 mg, 34%).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was successively washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-30% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-6c8b7671b03e4e098179b47fbd77e0e7
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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