Triethylamine → 3-chloro-1-(2-chloro-pyridin-4-yl)-1H-indazole

HRID 729526

反応式

HRID 729526 の反応式
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl.CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[CH:17]=2)[N:3]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 958943-Chloro-1H-indazoleHCID 51034082-Chloropyridine-4-boronic acid, pinacol ester

生成物 1

HCID 578326883-chloro-1-(2-chloro-pyridin-4-yl)-1H-indazole

試薬・触媒・溶媒 3

HCID 8895Cupric acetate触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-chloroindazole (1 g, 6.6 mmol) in methylene chloride (25 mL) and methanol (25 mL) were added 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (3.6 g, 15 mmol) and copper(II) acetate (1.4 g, 7.5 mmol), followed by triethylamine (2 mL, 15 mmol). The resulting mixture was vigorously stirred at room temperature for 20 h. The reaction was filtered and the gray solid was discarded. The blue filtrate was concentrated in vacuo and the residue was dissolved in methylene chloride and washed with saturated sodium bicarbonate and brine and dried over MgSO4. Flash chromatography of the crude product mixture with 25:10:65 and 35:10:55 EtOAc-CH2Cl2-Hexane gave the title compound as a white solid. MS (ES+): 264.0 [M+H]+.

後処理

  1. filtrationThe reaction was filtered
  2. concentrationThe blue filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-d3de64a78146454b9dbf70b4aff034af
出典データセット
uspto-grants-2009_09
特許番号
US07582631B2

関連ノート

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