Triethylamine → HCID 22472984, compound

HRID 2183738Notes

Reaction equation

HRID 2183738 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].[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.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:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)[N:15]=[CH:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 22472992HCID 22472992, compound

Product 1

HCID 22472984HCID 22472984, 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), 3-pyridylboronic 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 5-(5-Nitro-pyridin-2-yloxy)-1-pyridin-3-yl-1H-indazole.

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-76ab059f176040089b5e18475aa98446
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

Loading…