Ethyl Acetate → HCID 68620615, compound

HRID 407154Notes

Reaction equation

HRID 407154 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.[N+:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O.O>[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:7][N:8]3[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 66801751HCID 66801751, compound

Product 1

HCID 68620615HCID 68620615, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

The mixture of 1-tert-butyl 3-ethyl 6-bromo-1H-indazole-1,3-dicarboxylate (1.3 g), p-nitrophenyl boronic acid (666 mg), Pd (dppf)Cl2 (92 mg), and potassium carbonate (1 g) in N,N-dimethylformamide/water (4:1, 20 Ml) was stirred at room temperature for 24 h. Ethyl acetate and water were added. The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, EA only) to give 1-tert-butyl 3-ethyl 6-(4-nitrophenyl)-1H-indazole-1,3-dicarboxylate (1.3 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, EA only)

Sources & evidence

ORD record
ord-2e8d3af1b3304c7fb88a419c99f73781
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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