Dimethylformamide → HCID 68260424, compound

HRID 1802888Notes

Reaction equation

HRID 1802888 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 469419134-Bromo-5-methoxy-1H-indazole

Product 1

HCID 68260424HCID 68260424, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-5-methoxy-1H-indazole (8.57 g), ethyl bromoacetate (7.56 g), potassium carbonate (6.26 g) and N,N-dimethylformamide (30 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (4.65 g, yield 39%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 106-107° C. MS: 315 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-701237814f6a4a2284e9834fe333025b
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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