Toluene → 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate

HRID 347451ノート

反応式

HRID 347451 の反応式
[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][NH:12][C:11]2=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:21])=O.CCN(C(C)C)C(C)C.C1(C)C=CC=CC=1>C(OCC)(=O)C.O>[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2[Cl:21])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

参加物

7

反応物 4

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1356205694-Hydroxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate

生成物 1

HCID 210816794-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 5-methyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate (300 mg, 1.20 mmol), phosphorus oxychloride (2.0 mL, 21.4 mmol) and DIEA (0.5 mL, 2.80 mmol) was added toluene (10 mL). The reaction was heated at 110° C. for 4 hours and then cooled to room temperature. The mixture was diluted with ethyl acetate (10 mL) and water (5 mL). The organic layer was separated and dried with sodium sulfate, concentrated in vacuo and purified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2) to give the title compound (250 mg, 78%) as a white solid.

後処理

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-6c1996030b3b412ca996c70ff1ec672d
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

反応ノート

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