Nitrogen → HCID 10178724、化合物

HRID 1372523ノート

反応式

HRID 1372523 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 10178724HCID 10178724、化合物収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4cc91c2b123f446e8aa19bebeb142cc7
出典データセット
uspto-grants-2007_01
特許番号
US07157604B2

反応ノート

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