Nitrogen → HCID 10178724, 화합물

HRID 1372523노트

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HRID 1372523 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 10178724HCID 10178724, 화합물수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4cc91c2b123f446e8aa19bebeb142cc7
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157604B2

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