Methanesulfonyl chloride → 6-Chloro-3-[2-(5-ethyl-pyridin-2-yl)-vinyl]-1H-indazole

HRID 1827462ノート

反応式

HRID 1827462 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11](O)[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.S(Cl)(C)(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178436305HCID 178436305、化合物

生成物 1

HCID 693535806-Chloro-3-[2-(5-ethyl-pyridin-2-yl)-vinyl]-1H-indazole収率 79.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1-(6-Chloro-1H-indazol-3-yl)-2-(5-ethyl-pyridin-2-yl)-ethanol (232 mg, 0.60 mmol) in CH2Cl2 was added TEA (0.25 mL, 1.81 mmol) and mesyl chloride (0.070 mL, 0.90 mmol). The reaction was stirred for 30 minutes, and then DBU (2 mL) was added. The reaction was refluxed for 18 hours and then quenched with 40 mL of 1 N citric acid. The layers were separated, and the aqueous was extracted with 20 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (12 g silica gel, 50–70% EtOAc/hexanes) yielded the desired compound (135 mg, 71%).

後処理

  1. temperatureThe reaction was refluxed for 18 hours
  2. customquenched with 40 mL of 1 N citric acid
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with 20 mL CH2Cl2
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customPurification by chromatography (12 g silica gel, 50–70% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-6bf77448e5734500a5aa2f2c2616e2a3
出典データセット
uspto-grants-2006_05
特許番号
US07053107B2

反応ノート

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