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

HRID 729526

반응식

HRID 729526 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d3de64a78146454b9dbf70b4aff034af
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582631B2

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