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Dimethylformamide → 4-Ethyl-7,8-difluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-4,5-dihydropyrrolo[1,2-a]quinoxaline-1-carbonitrile

HRID 229375
ノート
印刷プレビュー

反応式

HRID 229375 の反応式
[CH2:1]([CH:3]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([CH3:24])[CH:17]=2)(=[O:15])=[O:14])[C:11]2[C:6](=[CH:7][C:8]([F:26])=[C:9]([F:25])[CH:10]=2)[N:5]2[CH:27]=[CH:28][CH:29]=[C:4]12)[CH3:2].ClS([N:34]=[C:35]=O)(=O)=O.CN(C=O)C>C1COCC1>[CH2:1]([CH:3]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([CH3:24])[CH:17]=2)(=[O:15])=[O:14])[C:11]2[C:6](=[CH:7][C:8]([F:26])=[C:9]([F:25])[CH:10]=2)[N:5]2[C:27]([C:35]#[N:34])=[CH:28][CH:29]=[C:4]12)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 690662264-Ethyl-7,8-difluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-4,5-dihydropyrrolo[1,2-a]quinoxaline

生成物 1

HCID 690613684-Ethyl-7,8-difluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-4,5-dihydropyrrolo[1,2-a]quinoxaline-1-carbonitrile収率 85%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-78 °C

実験手順

To a 250 ml round bottom flask with addition funnel was added 2 g (4.8 mmol) of the product from Example 4 and 50 ml of THF. The solution was cooled to −78° C. and 0.50 ml (5.76 mmol) of chlorosulfonyl isocyanate in 20 ml of THF added dropwise via the addition funnel. After the addition was complete the solution was stirred at this temperature for 3 hr until all of the product had disappeared by TLC. Added 1 ml of DMF and allowed the solution to warm to room temperature, whereupon product begins to form. After stirring overnight the reaction was quenched with saturated sodium bicarbonate solution, then extracted 3 times with ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to afford an oil, which was chromatographed on silica gel eluting with 30% ethyl acetate:hexane to afford 1.81 g (83%) of product as a solid, which was recrystallized from ethyl acetate hexane, mp 176-178° C.

後処理

  1. additionTo a 250 ml round bottom flask with addition funnel
  2. additionAfter the addition
  3. temperatureto warm to room temperature, whereupon product
  4. customto form
  5. stirringAfter stirring overnight the reaction
  6. customwas quenched with saturated sodium bicarbonate solution
  7. extractionextracted 3 times with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto afford an oil, which
  11. customwas chromatographed on silica gel eluting with 30% ethyl acetate

出典と根拠

ORDレコード
ord-a8c15035606d4d61bdf75fc955754974
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07563793B2

反応ノート

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