Nitrogen → HCID 10178724, compound

HRID 1372523Notes

Reaction equation

HRID 1372523 reaction equation
[C:1]([C:4]1[C:5](=[O:23])[CH2:6][CH2:7][C:8]2([CH2:19][CH2:20][CH2:21][CH3:22])[C:16]=1[C:15]1[C:10](=[CH:11][C:12]([NH2:18])=[C:13]([F:17])[CH:14]=1)[CH2:9]2)(=[O:3])[CH3:2].N#N.[Br:26]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([C:4]1[C:5](=[O:23])[CH2:6][CH2:7][C:8]2([CH2:19][CH2:20][CH2:21][CH3:22])[C:16]=1[C:15]1[C:10](=[C:11]([Br:26])[C:12]([NH2:18])=[C:13]([F:17])[CH:14]=1)[CH2:9]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 947NitrogenHCID 67184N-bromobutanimideHCID 179726764-acetyl-7-amino-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 10178724HCID 10178724, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-acetyl-7-amino-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (157 mg, 0.5 mmol) in anhydrous N,N-dimethylformamide (1.5 mL) was purged with N2, cooled in an ice bath, and treated with N-bromosuccinimide (89 mg, 0.5 mmol). The resulting solution was stirred at 0–5° C. for one hour, and then partitioned between EtOAc and water. The aqueous portion was extracted with more EtOAc. The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum. The oily residue was purified by flash chromatography on a Biotage 12M column, eluting with 4:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to afford 4-acetyl-7-amino-8-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (147 mg, 75%) as a yellow oil.

Workup

  1. temperaturecooled in an ice bath
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous portion was extracted with more EtOAc
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe oily residue was purified by flash chromatography on a Biotage 12M column
  9. washeluting with 4:1 hexanes-EtOAc
  10. additionThe product containing fractions
  11. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-4cc91c2b123f446e8aa19bebeb142cc7
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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