Triethylamine → HCID 11218363, compound

HRID 2242878Notes

Reaction equation

HRID 2242878 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[N:2]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 92211H-IndazoleHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 11218363HCID 11218363, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1H-Indazole (0.50 g, 4.23 mmol), 4-methoxyphenylboronic acid (1.30 g, 8.5 mmol), triethylamine (0.86 g, 8.5 mmol) and cupric acetate ((0.77 g, 4.23 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 48 h. The reaction mixture was diluted with water and passed through a pad of Celite. The filtrate was extracted with EtOAc, washed with brine, and dried over Na2SO4. After being concentrated, the crude material was purified by a chromatography on silica gel to yield the title compound (0.32 g, 30%).

Workup

  1. extractionThe filtrate was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter being concentrated
  5. customthe crude material was purified by a chromatography on silica gel

Sources & evidence

ORD record
ord-7b07ff04944c47b98429c18f7291f6a9
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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