Triethylamine → HCID 22472956, compound

HRID 2183733Notes

Reaction equation

HRID 2183733 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].C(N(CC)CC)C>CS(C)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:25]2[CH:26]=[CH:27][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)[N:15]=[CH:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343264-Cyanophenylboronic acidHCID 22472992HCID 22472992, compound

Product 1

HCID 22472956HCID 22472956, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-(5-Nitro-pyridin-2-yloxy)-1H-indazole (1.0 g, 3.9 mmol) in 15 mL of DMSO is added copper (II) acetate (0.71 g, 3.9 mmol), powdered 4A molecular sieves (0.2 g), 4-cyanophenylboronic acid (4.3 mmol) and triethylamine (2.7 mL, 20 mmol). The resulting mixture is stirred under an oxygen atmosphere for 3 days. After filtering through a plug of Celite and silica gel, the mixture is concentrated in vacuo, adsorbed to silica gel, and purified by column chromatography eluting with 0-20% ethyl acetate-hexanes, affording 4-[5-(5-Nitro-pyridin-2-yloxy)-indazol-1-yl]-benzonitrile.

Workup

  1. filtrationAfter filtering through a plug of Celite and silica gel
  2. concentrationthe mixture is concentrated in vacuo
  3. custompurified by column chromatography
  4. washeluting with 0-20% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-fa4aae69bdee4c7283645525a09c9971
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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