Triethylamine → 7-Bromo-2-isopropyl-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8260

反応式

HRID 8260 の反応式
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[N:20][N:19]4[CH2:28][CH2:29][CH2:30][C:18]=34)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>O1CCCC1.O>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[N:20][N:19]4[CH2:28][CH2:29][CH2:30][C:18]=34)=[CH:12][C:13]([CH:1]([CH3:3])[CH3:2])=[N:14]2)=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219925197-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolineHCID 178418918HCID 178418918、化合物

生成物 1

HCID 102247947-Bromo-2-isopropyl-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A 2 M solution of isopropyl magnesium chloride in tetrahydrofuran (65 μL, 0.13 mmol) is added to solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (50.0 mg, 0.13 mmol) in tetrahydrofuran (1 mL) at room, temperature with stirring for 2 h. The mixture is cooled to −78° C. and triethylamine (21.4 μL, 0.154 mmol) and methanesulfonyl chloride (11 μL, 0.14 mmol) added. The mixture is warmed to room temperature and allowed to stand 18 h. The mixture is treated with water, extracted with ethyl acetate, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (dichloromethane to 75% ethyl acetate/dichloromethane) to yield the title compound as a solid, 4.5 mg (9%).

後処理

  1. temperatureThe mixture is warmed to room temperature
  2. waitto stand 18 h
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (dichloromethane to 75% ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-b587c4a0071e4ce489f217f216631641
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

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