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

HRID 729526

Reaction equation

HRID 729526 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-d3de64a78146454b9dbf70b4aff034af
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Linked notes

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