Phosphorus oxybromide → HCID 57506731、化合物

HRID 1945580ノート

反応式

HRID 1945580 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-])=[CH:14][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:22])=O>C(#N)C.O1CCOCC1>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([Br:22])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 24613Phosphorus oxybromideHCID 59605785HCID 59605785、化合物

生成物 1

HCID 57506731HCID 57506731、化合物収率 72%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

A 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe and a condenser/inert gas bubbler (via a Claisen head), was charged with a solution of 1-benzenesulfonyl-1H-pyrrolo[3,2-c]pyridine 5-oxide (3.5 g, 12.8 mmol) in acetonitrile (50 mL) and dioxane (50 mL). To this solution was added dropwise phosphorus oxybromide (12 g, 40.9 mmol) and the resulting mixture was stirred at 70° C. for 18 h. The precipitate formed was removed by filtration and washed several times with dioxane. The solution was concentrated in vacuo and partitioned between DCM, water and brine. The organic layer was isolated then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane) to give the desired product (3.1 g, 72%). 1H NMR (CDCl3, 300 MHz): δ 8.23 (d, J=5.7 Hz, 1 H); 7.94-7.85 (m, 3 H); 7.67-7.59 (m, 2 H); 7.55-7.48 (m, 2 H); 6.75 (dd, J=3.7, 0.8 Hz, 1 H).

後処理

  1. customA 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe
  2. customThe precipitate formed
  3. customwas removed by filtration
  4. washwashed several times with dioxane
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between DCM, water and brine
  7. customThe organic layer was isolated
  8. dry with materialthen dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-7b750460254f4fde8e3621b75267726d
出典データセット
uspto-grants-2013_03
特許番号
US08394796B2

反応ノート

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