Diisopropylethylamine → 4,5-Dichloropyrrolo[2,1-f][1,2,4]triazine

HRID 2117124ノート

反応式

HRID 2117124 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=O)[NH:8][CH:7]=[N:6]2.C(N(C(C)C)CC)(C)C.O(Cl)[Cl:22].[P+3].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:22][C:9]1[C:10]2=[C:2]([Cl:1])[CH:3]=[CH:4][N:5]2[N:6]=[CH:7][N:8]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 1357420865-Chloropyrrolo[2,1-f][1,2,4]triazin-4(1H)-oneHCID 178479710HCID 178479710、化合物

生成物 1

HCID 210816694,5-Dichloropyrrolo[2,1-f][1,2,4]triazine収率 67.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 5-chloropyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (5.00 g, 29.5 mmol) in toluene (100 mL) at rt under nitrogen was added diisopropylethylamine (5.14 mL, 29.5 mmol) followed by phosphorus(III) oxychloride (8.25 mL, 88.5 mmol). The mixture was heated at 100° C. for 20 h and was then cooled to rt. The reaction was slowly added to saturated aqueous sodium bicarbonate solution (500 mL) at 0° C. After the addition was complete, the mixture was stirred at rt for 30 min. The aqueous phase was extracted with ethyl acetate (3×500 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (3.73 g, 67%) as a yellow solid which was used without further purification. 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.70 (d, 1H, J=2.8 Hz), 6.84 (d, 1H, J=2.8 Hz); MS(ESI+) m/z 188.1 (M+H)+.

後処理

  1. temperaturewas then cooled to rt
  2. additionAfter the addition
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eef68dead9064969a4b2d1a50ede38cd
出典データセット
uspto-grants-2008_10
特許番号
US07439246B2

反応ノート

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