Ethyl Acetate → methyl [3-(6-fluoro-3-iodo-1H-indazol-1-yl)propyl]carbamate

HRID 922463Notes

Reaction equation

HRID 922463 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[N:7][N:8]2[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 254236Methyl(3-bromopropyl)carbamateHCID 178505447HCID 178505447, compound

Product 1

HCID 68308666methyl [3-(6-fluoro-3-iodo-1H-indazol-1-yl)propyl]carbamateYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

to a solution of 6-fluoro-3-iodo-1H-indazole (1.5 g) and methyl (3-bromopropyl)carbamate (1.68 g) in N,N-dimethylformamide (5 mL) was added potassium carbonate (1.58 g), and the mixture was stirred at room temperature for 3 days. To the reaction solution was added ethyl acetate, and the mixture was washed with aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/20→3/2) to give methyl [3-(6-fluoro-3-iodo-1H-indazol-1-yl)propyl]carbamate [REx(102-1)] (836 mg) as a red oil.

Workup

  1. washthe mixture was washed with aqueous saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/20→3/2)

Sources & evidence

ORD record
ord-ca2fd1eb92a44d3d8714992967102056
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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