Triethylamine → HCID 22472972, compound

HRID 2183727Notes

Reaction equation

HRID 2183727 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].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(N(CC)CC)C>CS(C)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([O:10][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)=[CH:19][CH:18]=3)[CH:14]=[N:15]2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 22472992HCID 22472992, compound

Product 1

HCID 22472972HCID 22472972, compoundYield 20.5%

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 was added copper (II) acetate (0.71 g, 3.9 mmol), powdered 4A molecular sieves (0.2 g), 4-fluorophenylboronic acid (0.60 g, 4.3 mmol) and triethylamine (2.7 mL, 20 mmol). The resulting mixture was stirred under an oxygen atmosphere for 3 days. After filtering through a plug of Celite and silica gel, the mixture was concentrated in vacuo, adsorbed to silica gel, and purified by column chromatography eluting with 0-20% ethyl acetate-hexanes, affording 0.28 g of 1-(4-Fluoro-phenyl)-5-(5-nitro-pyridin-2-yloxy)-1H-indazole as a colorless syrup. 1H NMR (CD3OD, 400 MHz): δ 8.17 (s, 1H), 7.7-7.8 (m, 3H), 7.61 (d, 1H, J=2.8 Hz), 7.39 (d, 1H, J=2.0 Hz), 7.30 (m, 2H), 7.22 (m, 2H), 6.77 (1H, d, J=8.8 Hz) ppm.

Workup

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

Sources & evidence

ORD record
ord-e97b33729b3642b7975a2d169a5a36f9
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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