2-Fluoroethyl bromide → N1,N1-dimethyl-N2-([4-(2-fluoroethoxy)-2-methyl-2H-indazol-3-yl]sulfonyl}formamidine

HRID 1378933Notes

Reaction equation

HRID 1378933 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]=[N:4][S:5]([C:8]1[N:9]([CH3:18])[N:10]=[C:11]2[C:16]=1[C:15]([OH:17])=[CH:14][CH:13]=[CH:12]2)(=[O:7])=[O:6].[H-].[Na+].Br[CH2:23][CH2:24][F:25]>CN(C=O)C>[CH3:1][N:2]([CH3:19])[CH:3]=[N:4][S:5]([C:8]1[N:9]([CH3:18])[N:10]=[C:11]2[C:16]=1[C:15]([O:17][CH2:23][CH2:24][F:25])=[CH:14][CH:13]=[CH:12]2)(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 136000308HCID 136000308, compound

Product 1

HCID 86749619N1,N1-dimethyl-N2-([4-(2-fluoroethoxy)-2-methyl-2H-indazol-3-yl]sulfonyl}formamidineYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.2 g (15 mmol) of N1,N1 -dimethyl-N2 -[(4-hydroxy-2-methyl-2H-indazol-3-yl)sulfonyl]formamidine was added to a suspension containing 0.6 g (15 mmol) of 60% sodium hydride in 50 ml of DMF, and the mixture was stirred at room temperature for one hour. Further, 2 g (16 mmol) of 1-bromo-2-fluoroethane was added thereto, and the mixture was stirred at room temperature for 12 hours. The mixture was poured into ice water, and the formed crystals were collected by filtration and washed with water and IPE to obtain the desired product. This product was used for the subsequent reaction without purification. Obtained amount: 3.4 g (yield: 69.5%)

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. filtrationthe formed crystals were collected by filtration
  3. washwashed with water and IPE

Sources & evidence

ORD record
ord-3955f944978b4834917b6383f4f7562f
Source dataset
uspto-grants-1997_09
Patent number
US05670452

Reaction notes

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