2-Fluoroethyl bromide → HCID 18326216, compound

HRID 1250502Notes

Reaction equation

HRID 1250502 reaction equation
[SH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[N:8]=1)=[O:6].[H-].[Na+].Br[CH2:29][CH2:30][F:31]>CN(C=O)C.C(OCC)(=O)C>[F:31][CH2:30][CH2:29][S:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[N:8]=1)=[O:6]

Participants

6

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 15906612HCID 15906612, compound

Product 1

HCID 18326216HCID 18326216, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (0.0027 mol) of N-(2-mercaptoethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide (compound No. I-91) was dissolved in DMF, and the obtained solution was mixed with 0.12 g (ca. 60% in mineral oil; 0.0027×1.1 mol) of NaH and then with 0.68 g (0.0027×2.0 mol) of 1-bromo-2-fluoroethane, followed by stirring the solution for about one hour. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water and then washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. washwashed with saturated brine
  2. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0d9825d5e1184437a1bfd91982f9db52
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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